My Date - By Otkfme

• Part 12 - Marriage Proposal – Jane gets an engagement ring.
• Part 13 - New Years Eve – I get to spank Jane.
• Part 14 - New Years Eve cont. – Now Jane spanks me.
• Part 15 - Jane’s Secretary – Spanked by Jane’s secretary.
• Part 16 - Shopping with Jane – Spanked while shopping with Jane.
• Part 17 - Jane meets my parents – My mom shows Jane how to spank me.
• Part 18 - Back at Jane’s house – Jane just wants to spank me.
• Part 19 - Interview – I get hired to work at Jane’s company.
• Part 20 - Jane’s Shower – I get spanked at Jane’s shower.
• Part 21 - Bachelor’s Party – Jane gets a spanking.
• Part 22 - Wedding Night – We spank each other.

My Date - Part 12 - Christmas

It was Christmas time already. I had been dating Jane for over six months, and I was invited to a Christmas feast at her mom’s house. I was so glad that it was to be held at her mom’s house, instead of her sister’s , Connie, house. We were at Connie’s house for Thanksgiving, and I was later spanked by Connie in their special spanking room in the basement of her house.

We were suppose to be over to her parent’s house by noon, and Jane lived about a half an hour away. So Jane told me to pick her up at 11:30 AM. There was more traffic than I had anticipated, and I arrived at Jane’s house about five minutes late. I thought it wouldn’t be a big deal, being Christmas, but when I rang the doorbell and Jane yelled to come on in, she was standing there with a paddle in her hand.

“I thought you had changed so you wouldn’t be late, anymore. “ Jane said. “I know it’s Christmas and we are already late getting to my parent’s house, but you are still going to be spanked for being late. Since I want to get your spanking over with real fast, just drop your pants and under shorts, and bend over the table. Let’s see, five minutes late, that’s ten swats of the paddle.”

I had no choice but to follow her orders. “Yes, madam,” I said. At least this way, I didn’t have to spread my legs.

“You don’t have to count these out loud. SWAT You have been very good lately. SWAT And on time. SWAT I hope your SWAT behavior keeps improving. SWAT You have become SWAT very special to me. SWAT But don’t let that SWAT go to your head. SWAT Now stay in position until I say you can stand up.” SWAT.

“Yes, madam,” I answered. I stayed in position because I thought Jane just wanted to examine my bottom to see how red it was.

SWAT “Are you going to behave yourself at my parent’s house and not embarrass me?” SWAT.

“Yes, madam.”

SWAT “Because if you do, you can expect another spanking, right then and there. SWAT Do you understand, Clyde?”

“Yes, madam.”

SWAT “Good! You can stand up, now, and pull up your pants. Help me take these presents out to your car.”

So we loaded my car with her presents, and we drove over to her parents house. When we arrived, her sister, Connie, and Connie’s husband, Roger, were already there. I brought in Jane’s presents, and also the presents I had bought for her family. It was a spacious house, and they had a large Christmas tree. Many presents were already under the tree. As I was putting our presents under the tree, I saw many presents for me. That really showed me that I was becoming part of their family.

The table was all set, and her mother brought out the usual turkey, dressing, mashed potatoes, corn, etc for a Christmas feast. After Jane’s dad, George, said the prayer, I stood up and said, “I have a surprise for Jane and the family.” Jane was seated across from me, and I went to her chair and knelt down. “Will you marry me?” I asked as I pulled a diamond ring from my pocket.

“If I marry you, do you understand that you can expect spankings from me, my friends, my family, and my coworkers ’” Jane asked.

“Yes I do.” I answered.

“And you will willing submit to a spanking anytime, and anywhere I think you deserve one.”

“Yes I do,” I answered.

“Then, I guess I will marry you!”

Jane gave me a great big long kiss. She showed the nice ring I got her to the rest of the family. I was so happy! I didn’t necessarily liked to be spanked all of the time, but Jane and I got along so well. We shared the same likes and dislikes, and shared the same values. The family was happy, too. While we were eating, they all told me how wonderful it was going to be that I was going to be joining their family. I told them that I thought we should get married in about nine months, and that they would soon be meeting my family.

At this point, I thought this was turning out to be a wonderful Christmas. Jane had said that she would marry me, and her family accepted me. Then all of us gathered around the tree to open presents.

To my surprise, I got a lot of presents. Some were even from Jane’s coworkers. It was a bigger surprise once I started to open them. The first present was from Connie. It was a black riding crop. The second present was from her parent’s. It was a paddle with holes in it. The third present, that was from Jane, was a tawse. The fourth present was from Robin, Jane’s coworker, it was a cane. All of my presents turned out to be spanking implements.

After all of the presents were opened from under the tree, each person had to show what they got to the entire family. When it was my turn, I showed them all of the spanking implements.

“Jane will have a good time spanking you with those,” her sister said.

“Now you are really part of our family!” Her mother said.

“But wait a moment,” Her sister said. “Roger made a special present for Jane. Everybody wait here.” Then Connie and Roger went out to their van and brought in something that was covered with a sheet. “Jane, go ahead and take off the sheet and see what it is!”

When Jane uncovered it, it was a spanking bench like I was spanked on in Connie’s basement. It was made out of wood and it had places for your legs and arms. “Roger, tell them the new modifications that you have made!” Connie said.

“As you can see, it has wheels on it, so you can easily move it to where you want it. If you press this lever, the wheels retract and it sits on the floor. If you turn this wheel, it makes the arms and legs spread apart.” Roger reached into the middle of it and pulled out a small step stool. “It also has its own step stool. Also, you don’t need wristcuffs or ankle cuffs. The straps have velcro, so you can secure someone to this real fast.”

“Why don’t you try it out on Clyde right now.” Connie said. “This way we can also use the new spanking implements on him, that he just got.”

“Is it okay if I prepare Clyde for his spanking?” Jane’s mother asked.

“Sure,” Jane said. “Clyde, go over to mom.”

So I went over to Jane’s mom and she said, “Take off your shirt, shoes and socks. Then stand in front of me with your hands on top of your head.” After doing so she took down my pants and said, “It is going to be so nice that you are going to marry Jane and become part of this family.” Then she took down my under shorts. “Please turn around so that I can examine your butt.” Once I did she noticed that my bottom was pink from my earlier spanking from Jane. “What is this? Did Jane spank you before you came over here?”

“Clyde, go ahead and tell her,” Jane said.

“Yes, Jane spanked me,” I confessed. “I was five minutes late to her house so Jane gave me ten swats from her paddle, plus a few extras.”

“Well, I guess your bottom is really going to turn red after we finish spanking you.” Her mom said.

“Come over her so that we can secure you to this for your spanking.” Jane said. I went over to the wooden contraption, and climbed up the small step stool so that I was in position. It was like being on all fours, but in an elevated position. Jane and Connie immediately secured my knees, feet, elbows, and wrists to it.

“Let’s see how far we can spread his legs with this wheel,” Connie said. Then I felt the contraption moving, slowly spreading my legs further and further apart. Just when I thought my legs could not be spread apart anymore, it stopped. “That should about do it. You have full access to his body this way.” I felt someone grabbing at my penis and balls.

“Let’s start spanking him,” Jane said. Jane stood on one side of me and Connie the side. Each of them picked up a spanking implement and started to spank me. Each of them also told me what they were using. Jane’s mother also joined in in spanking me. Being in the position that I was in, with my legs spread, they spanked the tender insides of my legs and all of my bottom. I don’t think they left any part of my bottom untouched by the spanking. The spanking warmed up my bottom and started to really sting me. I started to try to move about and was starting to complain.

“Please, can you stop spanking me. My bottom really hurts!” I said.

“We have one last thing to try on you, and that’s the cane.” Jane said. “Connie, get a scarf. I want to make sure he doesn’t say a word while he is caned.” While Connie left the room to get a scarf, Jane reached under her skirt and pulled off her white cotton panties. “Open up your mouth!” Jane told me. Then Jane stuffed her panties into my mouth. Connie came back with a scarf, and the panties were secured with the scarf around my head. Then Jane said to Connie, “Why don’t you give Clyde six strokes of the cane.”

“Be happy to.” Connie said. She tapped my poor tender bottom, I heard a whistle, then CRACK. It felt like a line of fire on my bottom. I tried to free myself, but I was held securely in place.

“You now have a nice red straight line on your bottom,” Jane said. “Get ready for five more.”

CRACK. Again, a burning sensation. CRACK. Now my whole body felt like it was on fire.

“Your doing real good, Clyde. Only three strokes left,” Connie said.

CRACK. I wanted to rub my poor bottom. CRACK.

“Only one left. You now have five bright red lines on your bottom,” Jane said.

CRACK. Then I felt six hands feeling my bottom. “He probably will not want to sit down for awhile,” Connie said.

Then Jane said, “Once we release you, I want you to stand in the corner with your hands at your sides. Do not rub your bottom.”

I was released, but the panty gag was left in my mouth. Then I stood in the corner. I really wanted to rub my poor bottom, but I didn’t because I didn’t want a further spanking.

Then Connie said, “Now I want Roger up on this. Undress and then come over here for your spanking.”

While I stood in the corner, I could hear that Roger was being spanked, just like I was. After Roger was spanked, he had to stand in the corner next to me. Then George, Jane’s dad was spanked. Soon all three of us men were standing in the corner with bright red, stripped bottoms. The women sat around talking and enjoying themselves. They commented on how good our bottoms looked. They also said that this would be a truly red Christmas that the family would probably never forget.

Soon, we were allowed to get dressed and rub our spanked bottoms. Connie and Roger said that they would follow us to Jane’s house and deliver the spanking contraption. I thanked everyone for their gifts to me, and we left Jane’s parents house around five o’clock. I had to take it easy sitting down in my car seat. Jane gave me a big kiss and thanked me for the engagement ring. We finally arrived at Jane’s house, and I helped Roger unload the spanking contraption their his van. Then Connie and Roger went back to their house.

“Wasn’t it a wonderful Christmas,” Jane said. “I got an engagement ring from you. You got some great spanking implements that I can use on you. And I got this great spanking contraption, so that I can really give you a good spanking, anytime I want to, without going over to Connie’s house!”

I didn’t think that meeting Jane for the first time would lead to this!!!! What will happen next?


My Date - Part 13 - New Years Eve

For Christmas, I got many spanking implements from Jane’s family and coworkers. I also proposed to Jane, and Jane accepted. Jane also got a spanking apparatus from her sister. I also got spanked by all the women in Jane’s family, as well as all of the other men in Jane’s family. So to me, it turned out to be a different type of Christmas.

Now it was time to celebrate the New Year. Jane and I decided that we would celebrate it together, just the two of us. We could talk about our new engagement, and we could just be together.

I didn’t want to give Jane an excuse to spank me again, so I arrived on time to her house. Since we were engaged and all of that, Jane said that I could just ring the doorbell and let myself in. On the table by the couch were the spanking implements that I had received for Christmas and some ankle and wrist cuffs. We had decided to leave my spanking implements at Jane’s house, so I won’t have to transport them back and forth. In the middle of the living room were both the spanking apparatus Jane had received for Christmas and a wooden padded horse.

When Jane finally entered the living room, she looked beautiful! Her hair was real nice looking, and she had on a short tight dress.

“You look beautiful!” I said.

“I’m glad you noticed!” Jane said. Then Jane sat on the couch beside me.

“Since it is just the two of us alone together, I want to start out tonight discussing our relationship with each other.”

“I was hoping that you were going to say that. I feel that would be very important to me, too.” Jane replied.

“As you know, I love you very much. I have finally found someone who shares the same likes and dislikes, my same values, and is fun to be around.”

“I feel the same way, too.” Jane said.

“Because I love you so much, I have accepted being spanked by you, your friends, your family, and your coworkers. I do feel that these spankings have helped bring us closer together, and have enhanced our lovemaking.”

“I was hoping you would say that.” Jane said.

“At first I allowed myself to be spanked because I wanted to keep going out with you, but now they have taken on a deeper meaning. I feel that they show me that you really do care about me. That I am important in your life.”

“Yes, I agree.” Jane said.

“Now I know that you are the president of a club of women who likes to spank men, and you and your friends like to spank me. But remember that time I spanked you for being late for a date?”

“Yes I do.”

“You said you enjoyed being spanked, and liked the idea that I finally got up the nerve to spank you. Do you still feel that way?”

“Yes I do. I like being in control when I spank you, but I also liked it when you took control and finally spanked me.”

“As our relationship progresses, do you feel that we could share more in spanking each other. When I feel that you have been naughty, or haven’t done something right, would you accept a spanking from me?” I asked Jane.

“I guess it would be more of a balanced relationship that way. But as you agreed to when you proposed to me, I want to make sure you still agree to receive a spanking from me at anytime or anywhere. Otherwise this engagement is off.” Jane said.

“Yes, I still agree to be spanked by you, anytime or anyplace. But now, you would also accept a spanking from me, from time to time.”

“I would agree with what you said. It should bring our relationship closer together. It also should enhance our lovemaking.” Jane said.

“Then I propose, as a way to usher in the New Year and our new relationship, that you accept a spanking from me.” I said.

“Only if you agree to be spanked by me, afterwards.” Jane said.

“Sounds good to me! Also, why is the wooden horse still here? I thought Jane brought it over just for that spanking club you had?”

“Jane originally brought it over just for the meeting, but then she said that I could keep it. She knows how much I enjoy spanking you, so now it is mine.” Jane said.

“That’s good, because that’s what I want to use when I spank you. But first, I need to prepare you for your spanking. Please stand up." Then I stood up and went in back of her. I unzipped the back of her dress and helped her take it off. Next I unsnapped her bra in back, and helped her off with it. "Now put your hands on top of your head." Then I slowly grasped the waistband of her panties and pulled them down her legs. "Step out of your panties and then separate your legs." Then I put my hand between her legs and felt her sex. I wanted Jane to feel the same way that I feel when Jane examines me before a spanking.

I sat down on the couch, again, and said, "You can take your hands down from atop your head, but extend them out in front of you so that I may attach the wrist cuffs on them." Now Jane was all set to go over to the wooden spanking horse. "Follow me so that I can get you in position for your spanking." After we reached the wooden horse, Jane slowly bent over it. I first attached the wristcuffs to the legs of the wooden horse. "Spread your legs," I said. Then I secured her legs to the legs of the horse. Now Jane presented me with a pretty picture and the perfect target. With her legs spread apart, you could clearly see her sex, and her nice round bottom was raised up high.

"I'm going to start you out with the paddle that has holes in it," I said. I knew how it stung my poor bottom, and I wanted Jane to feel it, too.

SMACK Jane jerked a bit and said, "Ouch. That paddle really does sting." SMACK Jane moved around a bit more. SMACK "Are you done spanking me yet?" Jane asked.

"I have only just began," I replied. "Plus, your spanking rules for me should apply to you. Do not say anything unless you are asked to. Also, if you move around too much, I will increase your punishment."

"Okay, I guess so," Jane replied.

SMACK "Always address me as Sir, when I spank you, Jane."

SMACK "Yes, sir," Jane said. SMACK Jane wasn't moving about so much, now. SMACK It was nice to see her white bottom cheeks turn a nice pink color. SMACK

I put down the paddle and picked up the riding crop. WACK "Ouch. What did you change to?" Jane asked.

WACK, WACK "I told you not to speak unless spoken to. That is the riding crop." WACK, WACK, WACK.

Then I took the end of the riding crop and rubbed it against her sex. Jane wiggled about and sighed. WACK, WACK, WACK. Then I rubbed her sex with it, again. WACK, WACK, WACK.

This time I felt her sex with my fingers. I instantly felt her female dew on my fingers. Then I raised up the crop, again. WACK, WACK, WACK. Jane was now cooing and wiggling back and forth. WACK, WACK, WACK.

"Don't stop! Don't stop!" Jane yelled out. WACK, WACK, WACK.

Now her bottom was pink with red stripes. WACK, WACK, WACK.

Then I felt her sex with my fingers, again. I felt even more dew, and she shuttered and then relaxed while still secured to the horse. I immediately released her, she kissed me real hard, and then we went over to the couch and made love. It was quite the New Years celebration for me. It seemed like we could make love forever.

But then Jane got up and said,"Now it is time for me to spank you!"


My Date - Part 14 - New Year’s

It was New Years Eve. Jane, who I am engaged to, just let me spank her. This was different, because Jane usually spanks me. Anyway, after her spanking, she became very excited and we made love. I was hoping that we could make love into the New Year, but then Jane announced that it was my turn to be spanked. When we made love, both of us had no clothes on, so I was ready to be spanked.

Jane sat down on the couch and had me stand beside her. "Your spanking will be in three parts. First, I want you to bend over my knee for a hand spanking." I actually liked it when Jane spanked me this way. She would open her legs so that my penis was between her legs, and then she closed her legs again. This held me in place. Also, as she spanked me and I moved about, it was a real turn-on for me. I now had my feet on the floor and my hands on the floor in front of me.

Then my spanking started. SPANK "I am so glad we found each other," Jane said. SPANK SPANK "I really do like" SPANK to spank you", SPANK "and I think that you" SPANK "like to be spanked by me." SPANK "Is that correct, Clyde?" SPANK

Usually I liked being spanked by Jane. So I said, "Yes, madam." Jane always wants me to address her as madam when I am being spanked by her.

SPANK "And I also like it," SPANK "when you spank me now and then." SPANK "But I like it best," SPANK "when I am spanking you." SPANK

I guess that I have to admit that I do like being spanked by Jane more than when I spank her. But it is fun to switch places now and then. So I answered, "Yes, madam."

SPANK "I am so glad that I am engaged to you." SPANK "This way I will be able," SPANK "to spank you everyday." SPANK

I hadn't thought of that when I had proposed to Jane, but I answered, "Yes, madam."

SPANK "And now I will be able," SPANK "to bring in the New Year," SPANK "by spanking you." SPANK

Then Jane gave me about twenty spanks right in a row with no pause in between. I wiggled about a little bit, but she held me tight between her thighs.

"You can stand up now, Clyde." Jane said.

Jane then went into the kitchen and brought out a straight back wooden chair. "For the second part of your spanking, I want you to bend over the back of the chair and hold on to the seat." While I did so, Jane went over to the couch and reached under it. She pulled out a long bar with a cuff attached to each end. "That's right, you haven't seen this yet. All of the girls got together and gave me this as a Christmas present at work. It is called a speader bar. They had heard me complain that you don't always keep your legs spread when I spank you, so this solves the problem. What's even better, is that they got me two of these. That way when you come to see me at work, I can spank you with your legs spread apart there, too. So spread those legs!"

I guess it was true. Jane likes to spank me with my legs spread apart. But that makes me feel so exposed and vulnerable, So I tend to put my legs slowly together, again. I thought Jane never noticed that, but I guess she did. I was bent over the chair with my legs spread apart and Jane said, "Spread them a little more." Now my legs really felt spread apart. I next felt Jane put the anklets on me. "Now try to put your legs together." I tried and nothing much happened. Now my bottom was stretched wide apart for my spanking, and my penis and balls were hanging down between my legs. "I'm going to use the paddle with holes in it for this part of your spanking."

I hated that paddle, because it stung so much more than the others did. But then Jane started to spank me with it. After only a few swats of that paddle, I began to move from side to side. "Stay in one place, or you'll get even more swats from this paddle." So I did the best I could to stay still while Jane spanked me. After about ten minutes of this, Jane said, "Now I am going to use the wooden spoon on you. That way I make sure your whole bottom is bright red, even your most tender places."

Then I felt the spoon on the insides of my thighs, between my legs, and on the tender skin around my bottom hole. I was really getting a thorough spanking. My poor bottom felt on fire, all over. But then Jane quit spanking me. I felt her release my legs, and she said, "You can stand up now. Help me move the spanking contraption, that my sister gave me, in front of the television." I stood up, went over to the spanking contraption, put the wheels down, and rolled it in front of the TV.

"We have about ten minutes until midnight and the New Year. So hurry up and get on this, I will turn on the television, and I will count down the New Year by caning you." As I put down the wheels on the thing, Jane turned on the television. I pulled out the stool to climb up on it, and soon I was in place. Her sister's husband had made this as a Christmas present for Jane. It was made out of wood and was very ingenious. It was like being on your hands and knees in an elevated position. I put my elbows and knees down in these wooden boxes for them, and my arms and legs were strapped into place. Jane then turned a crank, which spread apart my legs even more. I wasn't looking forward to being caned in this position. I could see the TV and there was about two minutes until the New Year. Everyone was celebrating.

"When they get down to the final countdown, I am going to give you a stroke of the cane for every second starting at ten. Get ready to celebrate the New Year."

Of course I couldn't move, so I had to watch and wait. 60 seconds! "Be sure and countdown with me," Jane said.

Then Ten SWAT, Nine SWAT, Eight SWAT, Seven SWAT, Six SWAT, Five SWAT, Four SWAT, Three SWAT, Two SWAT, One SWAT, Happy New Year!!! SWAT.

My bottom felt like ten red hot rods had been laid on it. The cane had really stung my bottom. "You look real good with a nice red bottom, with eleven red stripes on it. This has truly been a wonderful way to celebrate the New Year for me." Jane said. "Don't you agree, Clyde?"

I didn't want anymore strokes of the cane, so I just said, "Yes, madam."

Then Jane cranked the thing so that my legs weren't so far apart. She released the Velcro straps that were holding me in place, and I climbed down from the contraption. Although my bottom was very tender, we made love, again, as we saw others celebrate the New Year on television. I sure will remember this New Years celebration for many years to come.


My Date - Part 15

It is now after Christmas, and I am now engaged to marry Jane. We had decided that I would pick her up at her work, right after I was done with my work. We didn't set any specific time, and we were going to go out to eat. I had tried to go out with her at noon one time, and I was so late showing up, Jane wasn't able to eat with me. She had to go to an important meeting. So I was hoping this would work out a lot better.

After I had arrived at Jane's company, I went directly to her secretary's office. Tami was her secretary's name, and she was about twenty-one years old. I had met Tami before, when came to have lunch with Jane.

"Is Jane in? She should be expecting me." I said.

"Jane said you probably would be by at the end of the day," Tami said. "She is out of her office right now, but she should be back, shortly. Here is a letter she left for me to give to you. Jane wanted me to make sure you read it, and that you follow her directions."

I opened the envelope that the letter was in, and the letter read as follows, "Clyde- I am looking forward to eating out with you. If you are reading this letter, I must not be back in my office, yet. Last time you came to the office, you were late, and I started to spank you. But then I was called away to a meeting, and I had Tami spank you. But Robin came in, and finished your spanking. But now, Tami wants to spank you, again, and complete your spanking. Please allow her to spank you, and follow all of her orders. I should be back, shortly."

I was looking forward to taking Jane out to eat. I didn't think that I would be spanked at her work. But I knew that if I didn't let Tami spank me, that I would get a real hard spanking from Jane later. I turned to Tami and said, "I read the letter and I understand that I am supposed to be spanked by you."

"That is correct. I never got to really spank you, the last time you were here." Tami said.

"Okay," I said. "How do you want to spank me?"

"I think I'll have you bend over the desk," Tami said. "But first, let me prepare you for your spanking. Please put your hands above your head and face me."

Then she came over to me and first took off my belt. Next, she unbuttoned my sacks, unzipped the zipper, and slowly pushed my slacks down to my ankles. Then I felt her fingertips in the waistband of my undershorts, and they joined my slacks at my ankles.

"Lift up one of your feet." I did, and then she first slid off my shoe, took off my sock, and slid off my slacks and undershorts from that leg. "Now the other leg." And she did the same thing to my other leg. I was now standing naked from the waist down in front of her. Although she had seen me naked before, at least then, Jane had me bent over her desk. "Let's complete this by taking off your shirt. Keep your hands on your head while I unbutton it for you." After my shirt was unbuttoned, Tami said, "You can remove your hands from your head and take off your shirt. Then bend over the desk for me and grab the other side."

Now I was completely naked, and bent over Tami's desk. "Stay there while I get some things from Jane's office." Off Tami went to Jane's office. When she returned, she put a bunch of paddles and spanking implements next to me. "These are some of your Christmas presents that Jane brought here from home. You must have had an unusual Christmas. Oops, I forgot something." Then she went back into Jane's office, again. This time she came out carrying the speader bar for my legs.

"Jane said to make sure I kept your legs spread with this. So spread your legs wide apart." I didn't like being spanked with my legs spread far apart. The speader bar allowed me to be spanked in my most tender parts, and it left my penis and balls hanging between my legs, out in the open. Tami connected the straps of the speader bar to my ankles, and now I had to keep my legs spread wide apart. Then I felt her fingers touch my penis and balls and Tami said, " I now see why Jane wanted me to use the speader bar, when I spanked you. Let's see. Last time I suppose to spank you for fifteen minutes. How about I spank you for fifteen minutes or until Jane comes back."

"Yes, madam," Is all that I thought I could say.

"I like the way Jane has trained you to be so respectful to women, especially while you are being spanked. I think I will start with this paddle."

Tami picked up a small paddle next to me, and then my spanking started, SPANK "I am so glad SPANK to hear that you SPANK are now engaged to Jane. SPANK I know that Jane SPANK enjoys spanking you SPANK and you must SPANK enjoy being spanked SPANK by Jane, SPANK It is also nice that SPANK Jane allows others SPANK to spank you. SPANK I hope to find SPANK a boyfriend SPANK that also allows me SPANK to spank him." SPANK.

Then I heard Tami's office door open. A female voice said, "I'm sorry to interrupt, but I have some important papers for Jane." This was so embarrassing for me, being completely naked, and being spanked by Tami, and having another female employee seeing me like this.

"Go ahead and put the papers on Jane's desk in her office. This is Clyde, Jane's fiancée', and Jane is letting me spank him." Tami said. She put her hand on the small of my back so that I would stay bent over her desk.

When the woman returned from Jane's office, she said, "I hope that I get a chance to get to know Clyde better, but right now I better let you continue with his spanking. Be sure Jane knows that I left her some papers."

"I'll do that," Tami said. The door closed again and Tami said, "That was Carol. She is another of the important women in this company. Carol, Robin, and Jane are the main women who run this place."

Then Tami put down the paddle she was using on me and picked up a paddle with holes in it. "But I better stop talking and continue on with your spanking."

Then SPANK, that paddle really stung me. I wiggled a little bit to shake off the sting. SPANK "I guess this paddle really SPANK makes as impression SPANK on you. SPANK I'll have to SPANK remember that if I get SPANK to spank you again." SPANK Now my bottom felt like it was heating up and becoming real tender.

SPANK "I see that SPANK your bottom is SPANK now turning red. SPANK I really do like SPANK this paddle." SPANK

Tami continued to spank me for another five minutes with this paddle. Then she exchanged it for a riding crop. She used that on the insides of my thighs, and even between my legs. Now my poor bottom was really warm and tender. After what seemed like an eternity of Tami spanking me with the crop, she finally laid it down and said, "I guess your fifteen minutes are up. Stay in position until I undo the leg speader." Then I felt her hands on my bottom. "Your bottom not only looks like it is red and on fire, but it also feels quite warm." I next felt her take off the straps that held my feet wide apart with the speader bar. I was finally able to put my legs together, again. "You can stand up, now. But Jane wants you to stand in one corner of her room when I am finished with your spanking. So follow me."

We entered Jane's office and Tami showed me the corner Jane wanted me to stand in. "Jane wants you to stand in this corner, with your arms at your sides. I will keep your clothes in my office. Jane should be here shortly." Jane's office door soon closed, and I was left in Jane's office, completely naked, with a red, well-spanked bottom.

In a few minutes, Jane's office door opened again. My back was towards the door, so I didn't know who entered. Then I felt hands on my bottom and a voice said, "This is Robin. I was in the same meeting that Jane was in, and she should be here shortly. In the meantime, I am going to sit down in a chair, and I expect you to come over to me and bend over my knees for a spanking."

Robin sat on a chair, hiked up her skirt, and soon I was bent over her knees. Robin said, "I see that SPANK Tami has done SPANK a good job in spanking you. SPANK I am also SPANK glad that you SPANK proposed to Jane SPANK on Christmas. SPANK It has made SPANK Jane very happy. SPANK I hope you will SPANK be stopping by SPANK the office, more often. SPANK so stand up SPANK now, and SPANK stand in the corner. SPANK SPANK SPANK Jane wants to see you in the corner when she comes back from her meeting."

So I stood up, and walked back to the corner, again. I heard Jane's office door open, again, and Robin said, "Stay there in the corner, and I hope to see you around the office more often."

Now my bottom was hurting, again, and it felt on fire. I kept my hands at my sides, and waited. After what seemed like an eternity, Jane's door opened again. This time Jane said, "I see that Tami gave you a good spanking. I hope that you have been a good boy, but before we go out, I want you to bend over the desk for ten swats of the paddle from me. So bend over the desk, now."

I wasn't looking forward to another paddling. When I turned around, Jane was standing there with a paddle already in her hands. "Do I have to? I just got a fifteen minute spanking from Tami and an over the knee spanking from Robin." I complained.

"Yes you have to. And for complaining, you will now receive twelve swats of the paddle."

So I bent over her desk for another paddling. "Spread your legs far apart and keep them spread. Otherwise, I will get the speader bar." So I spread my legs far apart and awaited my fate. Luckily for me, I didn't have to count the spanks. Jane spanked me swiftly without mercy. After I received my twelve swats of the paddle, she said, "You can stand up, now, and then go into Tami's office to get your clothes and get dressed. I will join you in a minute or two."

Then I went into Tami's office and got dressed. I felt really embarrassed having to ask Tami for my clothes and dressing in front of her. But soon Jane entered Tami's office, and then we left to eat out.

All I was expecting was to pick Jane up at her office and eating out. What I got was a spanking from three women. I never know what to expect. I better be in my best behavior when I eat with Jane.


My Date - Part 16 - Shopping with Jane

Since I am engaged to Jane, she thought it would be appropriate for me to go shopping with her. This way I would be able to get to know her tastes in colors and styles of clothes. Jane also told me that she would value what I thought about various outfits that she was going to try on. Also, I would find out her sizes, so I could buy her clothing in the future.

It was a Saturday and I was right on time when I picked her up at her house. We had the whole day to spend together, so there was no rush. We went to a large shopping center near Jane's house, with many, many stores. At first we went to general clothing stores, and Jane looked at light jackets, dresses and skirts. Jane bought some clothes that really looked good on her.

About two o'clock, we went to the food court and had a quick lunch, and then we were off shopping, again. This time we were going to stores that were exclusively for women. As the day was dragging on, I felt sort of out of place, and usually I was the only male in the store. It also seemed like Jane was taking more and more time in deciding what to try on. I was getting agitated, and was wanting Jane to quit shopping. I was hoping that her shopping spree would be over, and that we could start having fun, together.

Anyway, I started asking her, "Are you done, yet?" and "When will you be through?" and "Don't you realize what time it is?" and "Haven't you shopped enough for one day?" and so on.

Jane must have become very frustrated with my questions and my behavior because she sat down on a chair and said, "Clyde, come over here this instant. Put you hands above your head and don't say a word."

I did so and then Jane started to undo my belt, unzip my zipper, and drop my slacks. The women in the store began to gather around to see what was going on. Then Jane put her fingertips in the waistband of my shorts, and soon they were also at my ankles. I was so embarrassed! I was now standing naked from the waist down, in a women's store, with many women gathered around me.

"Bend over my knees for a spanking," Jane said to me. "I will not tolerate your questions and your behavior, when I am shopping!"

Jane proceeded to spank me in front of all of the women who were gathered around. Luckily for me, she was just using her hand. Spank, Spank, and Spank.

Then I heard a strange female voice say, "I'm a clerk here at the store. You are creating quite a scene and disrupting business. We have a backroom that is equipped to handle this behavior. Please quit spanking him, and follow me to this backroom."

"Clyde, get up for now. Pull your pants up, and follow the sales clerk to the backroom," Jane said.

I was happy for the spanking to be stopped, especially since so many other women were watching me being spanked. As I was following the sales clerk to the back room, the clerk said, "Now and then we get shoplifters in the store. This is where we interrogate them and sometimes even punish them." Then she opened a door and I was surprised what I saw. On the wall were some paddles and a cane. In the middle of the room was a pillory.

"We usually put suspected shoplifters in the pillory, that way we can do a comprehensive search of them." The sales clerk said. "Then if we find something, and we usually do, we tell them that we will either call the police or they can take a spanking. Most agree to the spanking. So you can use this room to spank him. There is no rush, we will be open for another three hours."

"Thank you very much," Jane said to the sales clerk. "I should be done spanking him in about a half hour. I'll let you know when I am done with the room."

"No rush," the sales clerk said. "Enjoy spanking him." Then she walked out of the room and shut the door.

"Clyde, go over to the pillory and stick you hands and head in it." I did so and soon I was secured in the pillory. They were low enough so that I had to bend over at my waist. Then I felt Jane take down my slacks and under shorts, but this time I had to step out of them. "Spread your legs for me." Now I was in a position like how Jane likes to spank me. I was naked from the waist down, bent over with my legs spread apart, and secured so I couldn't move.

"Now I will be able to give you the thorough spanking that you deserve. I want to make sure that if I take you shopping with me again, you will never behave like you did today. Do you understand?"

"Yes, madam," I replied. I never expected this when Jane and I entered this store. Then my spanking started again. Jane paddled me and paddled me. The pillory did a good job of keeping me bent over and in position.

After about twenty minutes of my spanking, I heard the door open. The sales clerk said, " I see his spanking is going well. His ass is a nice red color." I felt so embarrassed, having this young sales clerk looking at me.

"Would you like to spank him?" Jane asked the clerk.

"I would love to. Very rarely do we catch a man shoplifting in the store. This should be fun!" The clerk said.

Then she started to spank me. She paddled me as hard as what Jane had been paddling me. I could tell that she was an experienced spanker because she paddled me on the insides of my thighs and even between my legs.

After about ten minutes of her spanking me, she said, "Thank you for letting me spank him. I need to get back to the sales floor. I'll see you later."

Then Jane said to me, "Clyde. Thank her for spanking you."

So I regrettably said, "Thank you for spanking me."

"I was happy to help you out. See you later." Then the sales clerk left the room again.

"For the last part of your spanking, and since they have a cane on the wall, I will give you six strokes of the cane. Please count them out loud for me."

My poor bottom was already hurting, so I wasn't looking forward to the cane. At least I was held in place by the pillory. I felt Jane tap my bottom with the cane, the whistle, then SWAT.

"One. Thank you, Jane." It felt like a hundred bees had stung me in a straight line. SWAT.

"Two. Thank you, Jane." It really hurt. I really don't like it when Jane uses a cane on me. SWAT.

"Three. Thank you, Jane." I started to sway my hips back and forth to get rid of the pain.

"Quit moving," Jane said, "Unless you want an extra stroke." So I quit moving. SWAT.

"Four. Thank you, Jane." Now it felt like I won't be able to sit down for a week. SWAT.

"Five. Thank you, Jane."

"Only one stroke left," Jane said. "You are taking your spanking very well." SWAT.

"Six. Thank you, Jane." Then I felt Jane's hands feeling the six welts from the cane.

"That should make sure you never misbehave when you go shopping with me." Jane then came around in front of me and gave me a kiss. I was next released from the pillory.

"You can pull up your pants, now. I am not done shopping in this store. So you better behave, or I will pull you in here, again, for another spanking." Jane said.

Then we left the backroom, and Jane continued her shopping. When I saw the sales clerk, again, she said, "I see that she is done spanking you." She said it out loud, and many of the women in the store looked at me and smirked. "I was happy to help her out with your spanking."

I was so happy when we left that store. Jane said that when I proposed to her, that I could expect a spanking anytime and anyplace she decided to spank me. I didn't expect this!


My Date - Part 17 - Jane meets my Parents

I got engaged to Jane on Christmas Day. I have met her parents and her sister, but Jane has never met my parents. They live in another city, and I decided to fly Jane and myself down to see them. That way they would have a chance to talk with Jane and to get to know her before the wedding. Jane is such a wonderful woman, and we both agree on many of the same things. I am really looking forward to be married to Jane.

The flight went well, my parents picked us up at the airport, and my parents had the spare bedroom set-up for us to sleep in. We arrived on a Sunday, and had a big dinner together. It was great to see that Jane had a good conversation going with my parents. My parents seemed to like Jane, and Jane looked like she was enjoying herself.

Then came Monday morning. My dad left the house early, since he had a part-time job. So that left only Jane, my mom, and myself. I am used to sleeping in a queen size bed all by myself, and Jane is too. The bed we were sleeping on was just a regular size bed, and up until now, Jane and I had never really slept together. I had stayed overnight and made love to Jane, but we had never really slept together. So this was a new experience for both of us.

I have a tendency to roll around a lot when I sleep and I guess Jane likes to sleep in one spot. When I finally woke up, all of the covers were on my side of the bed, and Jane was already awake. I guess she didn't sleep to well because she had a mad expression on her face. I have seen that expression before, and that is usually right before Jane spanks me.

"Well, I see that you are finally awake. Do notice that I have NO covers on my side of the bed?"

"I guess so," I said.

"And do you know who rolled around in the bed and kept me awake most of the night?"

"Did I do that?" I answered.

"If we are going to get married, and sleep together, your night behavior needs to change. I know we will probably be sleeping on a larger bed, but your night time behavior needs to change, and I need you to change, now!"

Then Jane got off the bed and went over to her suitcase. She pulled out several paddles and a hairbrush. Now I knew that Jane was going to spank me.

"Can't this wait until we get back home?" I pleaded. "What if my mom hears you spanking me?"

"I don't care if your mom does hear me spanking you! You deserve a good spanking right now, and that's what you're going to get." Jane sat down in the middle of one side of the bed. "Come over here so that I can prepare you for your spanking." I had on only pajama bottoms, and soon they were at my feet and Jane had me step out of them. "Now lay over my lap for your spanking."

So I stretched out on the bed, with my bottom over Jane's lap. Jane immediately opened her legs and pinned my penis between her thighs, to hold me in place. The paddles and hairbrush were on the bed in plain view for me to see. That way I could see which one Jane was going to spank me with. "Do you have to spank me?" I pleaded.

"That is the only way I know that really changes your behavior." Jane answered. "Besides, I need to make sure I sleep well tomorrow night, without you taking away all of my covers. So get ready to get a red bottom." Jane picked up the paddle, then SPANK, SPANK, SPANK. Usually Jane starts softly and the spanks get harder as she goes along, but this time she was giving me a hard paddling. SPANK, SPANK, SPANK. I started to squirm around on her lap.

"You better lie still and not move about so much, or I will spank you all morning." Jane said. Although the paddle really stung my bottom, I held as still as I could. SPANK, SPANK, SPANK. This went on like this for about ten minutes, then Jane switched to the hairbrush and then to the other paddle. This paddle made a lot of noise, and really stung my poor bottom.

I heard the bedroom door open and my mother stuck her head in and said, "I don't mean to interrupt anything, but breakfast will be ready in five minutes. You don't have to get dressed. You can just put your robes on over your pajamas." Then my mom closed the door. I felt so embarrassed, knowing that my mom had seen Jane spanking me.

SPANK, SPANK, SPANK. "You are lucky that your mom has breakfast prepared for us already. Otherwise, I probably would have spanked you for another fifteen minutes." Jane said. SPANK, SPANK, SPANK. "Get up, now, and put on your pajamas, so we can eat breakfast with your mom."

I was thankful that Jane had quit spanking me. My bottom was sore and I was hungry for breakfast. I put on my pajamas, and Jane and I put on our robes and went to the kitchen. My mom had prepared toast, bacon and eggs for our breakfast. It was already on the plates and we sat right down and I ate real fast, since I was hungry.

As I was finishing up my breakfast, Jane and my mom were engaged in girl talk. But soon my mom asked, "Did I see you spanking my son this morning?"

"Yes you did. I started spanking Clyde on our fourth date. He was always late, and spanking him did finally change his behavior. In fact, I spank him whenever he does anything that annoys me. Last night he took all of the covers off my side of the bed. Tonight, he will probably not pull that stunt, again." Jane moved my empty plate off the table and said, "Take off your robe, drop your pajama bottoms, and bend over the table. That way your mom can see the results of your recent spanking."

I really didn't want to do it, but I knew that if I didn't follow Jane's orders, I would get another spanking. So I reluctantly took off my robe, dropped my pajama bottoms, and bent over the table.

"You did a good job of reddening his bottom." My mom said. "I haven't spanked Clyde since he was sixteen years old. I thought he was too old for a spanking, but apparently not. I know a spanking always improved his behavior. I guess it is good that you spank him."

"Yes, it really does improve his behavior." Jane said.

"I just wish that I had met you sooner. We have so much to discuss about Clyde and you. Especially since you are already engaged." My mom said.

"Do you want to spank Clyde for not bringing me over to visit you sooner?" Jane asked. "He is in the proper position for another spanking. Shall I get a paddle from the bedroom?"

"Yes, I do want to spank him." My mom said. "But I have my own paddle in the kitchen." My mom went over to the stove, and got down the paddle she had hanging on the wall. This is the same paddle that my mom had used on me when I was growing up.

"Spread your legs," Jane said. "That way your mom can spank you in all of your tender spots."

So I spread my legs and my spanking began again, but this time by my very own mother. SPANK, SPANK, SPANK. My bottom was already tender from my previous spanking, so this spanking really hurt. SPANK, SPANK, SPANK "I want you to bring Jane over to see us more often!" My mom said. SPANK, SPANK, SPANK "Is that understood?" SPANK, SPANK, SPANK.

"Yes, mother." I replied.

SPANK, SPANK, SPANK. "Jane must really care about you, if she spanks you." My mom said. SPANK, SPANK, SPANK. "And I hope she never stops spanking you." SPANK, SPANK, SPANK

"I intend to keep on spanking Clyde now and when we are married. He is such a bad boy, sometimes." Jane said.

SPANK, SPANK, SPANK. "Well, I am glad to find out that spanking him really improves his behavior." My mom said. SPANK, SPANK, SPANK. My mother quit spanking me and I felt her hands on my burning bottom. "That spanking should last you for a while. Why don't you go to your room, shower, and get dressed? Jane and I have a lot to talk about."

"Yes, that’s a good idea." Jane said. "It will probably be hard for you to sit down comfortably for today. Your bottom is really red, now."

So I left to shower and to get dressed while Jane and my mom talked about spanking me and my bad behavior. This is not what I expected to happen when brought Jane over to meet my parents.


My Date - Part 18

Well, Jane had finally met my parents. Although Jane and my mom had spanked me while we were visiting my parents, I still felt that it was a good trip. It seemed like Jane and my mom got along very well. In fact, my parents are now looking forward to seeing us before our marriage ceremony.

Our flight back was a smooth one, and we got back to Jane's house about noon on Sunday. I carried Jane's suitcase into her living room and was ready to kiss her and head back to my place when Jane said, "Don't be in a hurry to head back home. I have some plans for you! Please wait here in the living room."

I always look forward to be with Jane. We enjoy each other's company, we agree on so many things, and I am looking forward to being married to Jane. To my surprise, Jane brought out the wooden spanking horse that her sister's husband had built for her.

"You aren't going to spank me, are you?" I asked.

"Yes, I am going to spank you." Jane replied. "Although you may not deserve a spanking that much, you agreed when you proposed to me that you would accept a spanking from me at anytime and at anyplace. I just feel like spanking you right now! So take off your shoes, socks, and shirt. Then I will further prepare you for your spanking. But first, I need to get the spanking implements that I will use on you."

As I was taking off my shirt, shoes and socks, Jane came out with two paddles, a hairbrush, and the dreaded cane. Now I knew I was going to get a very sound spanking.

Jane came over to where I was standing and said, "Put your hands on top of your head." Then she unbuckled my belt, unzipped my zipper, and pulled my pants down. I always feel like a little boy when she strips me like this. I stepped out of my slacks and soon her fingers were in the waistband of my shorts. I soon was stepping out of them and now I was totally naked before Jane.

"I am so glad that you accept these spankings from me." Jane said. "It shows me that you really love and trust me."

"I do really love you!" I replied.

"I'm looking forward to spanking you throughout our upcoming married life." Jane said. "So go over to the spanking horse and bend over it."

At least the spanking horse was padded on the top. I bent over it and Jane was soon securing my wrists to the front legs of the wooden horse. Then she said those dreaded words, again. "Spread your legs so that I can secure them to the legs of the horse." I always feel so vulnerable with my legs spread like that. It exposes the tenderest parts of my bottom, and it makes my penis and balls totally hang out. Also, when I am secured like this, there is no way that I can rub my bottom. I think Jane likes it because it keeps me in place.

Then she put down the paddles, hairbrush, and cane next to my head so that I can see them. "This way you can see what implement I am using to spank you with." Jane said. Jane picked up one of the paddles and said, "I had a nice discussion with your mother about spanking you. We both agreed that you should be spanked more often. So this is a spanking so that you can remember taking me to meet your parents. I am so glad that I am going to marry you, and you look so cute with your bare bottom up in the air, ready to be spanked. Don't you agree, Clyde."

"Yes, madam." I replied. This is the response Jane always wants to hear when she spanks me. If I reply any other way, I will receive an even more severe spanking. I really do look forward to marrying Jane, but not necessarily being spanked like this.

Then my spanking began. SPANK, SPANK, SPANK. Jane is real good about alternating between cheek to cheek. I always get a through spanking from her. My poor bottom always hurts all over by the time she is done with my spanking. SPANK, SPANK, SPANK.

"I like the way your bottom changes in color when I spank you," Jane said. SPANK, SPANK, SPANK. "It's turning a nice pink color right now." SPANK, SPANK, SPANK.

"Yes, madam." Is all that I could say in my reply. SPANK, SPANK, SPANK.

Jane spanked me about ten minutes with this paddle then said, "Now it is time for the hairbrush." I saw her lay down the paddle and pick up the hairbrush. SPANK, SPANK, SPANK. The hairbrush tended to hurt more in a concentrated spot than the first paddle. SPANK, SPANK, SPANK. When Jane spanks me with the hairbrush, she often pulls back one of my cheeks so that she can spank me in my most tender parts, between my cheeks. SPANK, SPANK, SPANK. This way I feel the spanking for several days. SPANK, SPANK, SPANK.

After she spanked me with the hairbrush for about five minutes, Jane put down the hairbrush and picked up the other paddle. This paddle had holes in it and it really stings me. "This paddle should turn your bottom from a nice pink color to a bright red color." Jane said. SPANK, SPANK, SPANK. Not only did it really sting my bottom; SPANK, SPANK, SPANK, but it also made my bottom feel very warm. SPANK, SPANK, SPANK. Although I my wrists and ankles were secured to the wooden horse, I tried to move around a little to get away from the paddle. SPANK, SPANK, SPANK. "Don't move about so much, or your spanking will even last longer."

"Yes, Madam," I said. SPANK, SPANK, SPANK. I held as still as I could with that stinging paddle hitting my bare upturned bottom. SPANK, SPANK, SPANK.
Jane finally quit spanking me with the paddle, and she grabbed the cane. "Since you have been very good to me on this trip to see your parents, I'm only going to give you six strokes of the cane."

"Yes, Madam," I replied. I didn't even like receiving one stroke of the cane. It always leaves welts, and sometimes I can see them for several days.

"Be sure and count them out loud for me!" Jane said. After I would count each stroke, Jane also has me thank her. Sometimes I don't feel like thanking her after a painful stroke, but if I don't, the stroke doesn't count, and I am given it again.

Jane taps my bottom with the cane, I hear the familiar whistle, and then I feel the cane. It feels like a red-hot iron has gone across my bottom. The first and last strokes always seem to hurt the most. "One. Thank you, Jane." I say. Now I have only five strokes left.

Tap, whistle, sting! "Two. Thank you, Jane." Jane is real skillful with the cane. The strokes are always parallel and spaced about an inch apart.

Tap, whistle, sting! "Three. Thank you, Jane." Now I only have three strokes left.

"I'm almost done with your spanking," Jane says. "You always take your spankings very well."

Tap, whistle, sting! "Four. Thank you, Jane."

"This one is going to land in the crease between your bottom cheeks and your thigh. Get ready for it."

It hurts a lot when she gives me the cane in that spot. I can feel it afterwards, when I walk or sit down. Tap, whistle, sting! "Five. Thank you, Jane."

"Now here is your last one." Jane says.

Tap, whistle, sting! "Six. Thank you, Jane."

"Now stay in place while I get some cream for your poor red bottom."

I'm still secured to the wooden horse, so of course I'm not going anywhere. Soon Jane returns and rubs the cream on my bottom. It feels so cool and nice, and it is exciting to have here hands all over my bottom, and sometimes going between my legs with the cream.

Then Jane released me from the spanking horse. She continues to sooth my tender bottom with her hands. Soon we find ourselves rolling around on her living room floor, making love to each other. Yes, I will remember this spanking and the trip with Jane where she got to meet my parents.


My Date - Part 19

I was at work, recently, when Jane called me on the phone.

"Can you please pick me up at work before 5 o'clock. I would like to go out to dinner with you and discuss a few things."

With our wedding coming up in a few months, I knew we had a lot to discuss, so I told her that I would be there before 5 o'clock. I took off of work a little early, and was proud of myself for getting to her office before four-thirty. You need to go through Jane's personal secretary's office to get to her office. When I entered her secretary's office, there was a new woman who I had never met before.

I said to her, "Hi. I don't think we have met before. I'm Clyde, Jane's fiancé, and Jane is expecting me. And what is your name?"

"I'm Cindy. I started working for Jane just last week. She said that you would probably stop by around five. Jane is in a meeting somewhere else in the building, but she left this note for you to read. I'm suppose to call Tami, her old secretary, once you arrive. Please sit down."

Cindy got on the phone to Tami while I read the note. The note reads like this, "By now, you have met my new secretary, Cindy. Late or on time, I want Tami to teach Cindy how I want you spanked when you come over to my office. My meeting should be over with a little after five, and then I can finish your spanking and we can go out to eat. See you shortly. Jane."

I made an effort to be on time, and I was hoping I wouldn't be spanked, especially by a woman I have just met. But this is what Jane wants, so I guess I get another spanking. "Tami will be down here in a few minutes," Cindy said. Cindy looked to be about twenty years old, with a short dress, and a nice smile.

Soon Tami walked into Cindy's office. "Hi, Clyde." Tami said. "I have been promoted so I am no longer Jane's secretary. I am now Robin's personal secretary. Jane wants me to show Cindy how Jane wants you spanked, so you can start by taking off your clothes except for your under shorts."

I started to get undressed and Tami said to Cindy, "Let's go into Jane's office while he is getting undressed. I'll show you where she keeps the paddles and stuff." So I put my clothes neatly on a chair and waited for them to come out of Jane's office. Soon the door opened again, and each of them was carrying two paddles.

"Cindy, sit on a chair, and Clyde, go over and stand in front of her with your hands on your head." I was now standing in front of Cindy in only my under shorts and Tami continued to say, "This is the part that is really embarrassing to Clyde. Slowly pull down his under shorts, help him step out of them, then tell him to bend over your desk."

Soon I was standing completely naked in front of a young woman that I had just met. Then Cindy said, "Now bend over my desk for your spanking." I was now in position to be spanked by Tami and Cindy.

"Jane likes him to spread his legs apart. That way you can spank the tenderest part of his bottom, and you can also tease him by grabbing a hold of his cock and balls. So Clyde, spread your legs apart." Tami said.

With my legs now spread wide apart, next I was feeling both Tami's and Cindy's hands between my legs. "Clyde is now ready to be spanked. Lets each grab a paddle and spank him. Jane always wants him spanked enough so that his bottom turns pink, but not much more. That is because Jane will spank him, herself, once she returns. You should try to spank him all over, not just in one spot."

Then my spanking began. Cindy stood on one side of me and Tami was on the other. They alternated between spanks, so I got a fast and furious spanking. After about ten minutes of this, Tami said, "We should stop spanking Clyde, now. See how pink his bottom has become. Don't be afraid to feel his bottom after you have spanked him. Clyde knows to stay bent over the desk until you tell him he can stand up." Then I felt four hands on my bottom. It really felt good compared to their stinging paddles.

"You can stand up, now, Clyde, and stand in the corner in Jane's office." Tami told me. As I stood in the corner of Jane's office, Tami said to Cindy, "This is when you put all of Jane's paddles on her desk. You leave Clyde's clothes in your office. That way, he can't easily get dressed. Then you wait for Jane to get back from her meeting. Jane will spank Clyde one more time." Then Tami said to me. "Clyde, I will miss spanking you at the office, but I have a feeling that I will still get an opportunity to spank you occasionally." Then Tami and Cindy left the room.

When I heard Jane's office door open, I was hoping that it was Jane. But her walk was different and she had on a different brand of perfume. She walked over and stood next to me, looked me over and said, "My name is Nancy. I am from the HR department and Jane said that I would find you in her office like this. Jane wants me to talk to you about a few things, but first you are to go and bend over Jane's desk. You are to be spanked as I talk to you. So bend over Jane's desk."

Now I was about to be spanked by another woman I had just met. Nancy picked up a paddle from Jane's desk and said, "Jane tells me," Spank, Spank, Spank. "That you work for a computer company." Spank, Spank, Spank.

"Yes, madam." I replied. This is how Jane wants me to reply to her or other women who spank me.

Spank, Spank, Spank. "And that you are very good with computers." Spank, Spank, Spank.

"Yes, madam."

Spank, Spank, Spank. "Jane thinks that it would be nice if both of you worked at the same place." Spank, Spank, Spank. "You would be working here, helping us with our computers." Spank, Spank, Spank. "Does that sound good to you?" Spank, Spank, Spank.

"Yes, madam."

Spank, Spank, Spank. "You would get a raise in pay compared to your other job," Spank, Spank, Spank. "A free parking space," Spank, Spank, Spank. "And be able to work at the same location and hours as Jane." Spank, Spank, Spank. "Does it sound good to you?" Spank, Spank, Spank.

"Yes, madam."

Spank, Spank, Spank. "This will also give Jane and the other female personnel in the company an opportunity to spank you anytime they felt you need to be spanked." Spank, Spank, Spank. "Is that understood?" Spank, Spank, Spank.

I hesitated. I really didn't want to be spanked on a daily basis, but it would mean more income and Jane and I would be working the same hours at the same location. Spank, Spank, Spank. "Yes, madam."

"Good. I'll leave the papers to be filled out," Spank, Spank, Spank. "On Jane's desk. You can give your two-week notice at where you are currently working," Spank, Spank, Spank. "And I look forward to see you working here in two weeks." Spank, Spank, Spank. "You will make a good addition to our staff." Spank, Spank, Spank.

"Yes, madam."

Spank, Spank, Spank. "Yes can stand up, now, and go over and stand in the corner, again." As I went over to the corner, she said, "Your ass looks a nice bright red color. I look forward to spanking you some more!"

Then Nancy left Jane's office. Now my poor bottom felt quite warm and hurt a little. Jane's door opened again. This time it was Jane. "Come over to my desk and bend over it," Jane said. After I was bent over the desk, Jane said, "It looks like Tami and Cindy did a good job of spanking you. Did you get to talk to Nancy from the HR department?"

"Yes, madam."

"And did she also spank you?"

"Yes, madam."

"So will you be working here with me?"

"Yes, madam."

"That is good you made that decision. Since your bottom is red already, I'll spank you a few more times, then we can go out and eat, and discuss this further." Spank, Spank, Spank. Then Jane spanked me for about five minutes. By the end of her spanking I was moaning and squirming about.

"You can stand up, now, and get dressed. I'll be with you in a few minutes." Jane said.

Then I went into Cindy's office to get dressed. "Let's see your red bottom." Cindy said. So I turned around for Cindy. She rubbed my bottom with her hands and said, "Your bottom feels real warm, too. It looks like Nancy and Jane spanked you real well. I look forward to you working here with Jane."

I wasn't sure how to take that comment, but I just said, "Yes, madam," and got dressed. Jane soon came out of her office and we went out to eat. My first date with Jane has now blossomed into something I never expected.


My Date - Part 20 - Jane's Shower

I started to date Jane about a year ago. I knew that we were meant for each other from the first moment we met. We agree on so many things, and we enjoy being with each other. On my third date with Jane, she spanked me because I was late in picking her up. Since then, her mom, sister, and friends have spanked me. It is very embarrassing to be spanked by other women, but for me to keep my relationship with Jane, that is what she wants to happen to me. I love Jane that much. I recently got hired by Jane's company to help with their computer systems, and now I am even spanked by Jane and her other employees while at work.

Anyway, our wedding date is soon approaching. Jane scheduled a wedding shower and invited her family and friends to it. Jane invited relatives from three different states to attend the wedding shower and our wedding. In fact, so many people were invited to the wedding shower that Jane decided to hold it in a large conference room at the company where she works. What was strange for me is that Jane said that I should also attend the shower. This way I would have more time to meet her out of town friends and relatives, other than just at the wedding.

The shower took place on a Sunday afternoon. The first ones to arrive were her sister Connie and her nom, Kathy. Soon, all of the other guests arrived and they all had presents for Jane. Everyone was seated in a large circle so that everyone could see everyone. Jane started out by introducing me to the group of women, and then she took out a large armless chair and put it in the middle of the room. Then one by one, they presented Jane with their gift, and she opened it and thanked them.

The first few gifts were girlish things like soap and candles, but the next gifts were surprising to me. They consisted of paddles, crops, and other spanking implements. What was even more surprising to me were that a lot of these spanking implements were coming from her out of town friends and family. Jane must have told them that she spanks me.

After Jane had opened all of the gifts, she thanked everyone and said that it was time for refreshments and to talk to each other.

"Don't you think you should try out some of your gifts right now!" A woman in the group yelled out.

"Clyde is here, and all of us know that you spank him!" Someone else yelled out.

"This isn't what I had in mind when I invited you to this shower." Jane said.

Then a lot of comments came from the group like, "Please spank him." "We want to see Clyde spanked." And "Clyde needs a spanking."

I wanted to get to know Jane's friends and family a lot better, but not in this way. I felt so embarrassed, I wanted to quickly leave the room but the door was on the other side of the room. Soon the women were pulling my arms and pushing me into the middle of the room where Jane was seated.

"Clyde, come over here so that I can prepare you for your spanking." Jane said.

The room one women clapped and cheered, and then they pulled their chairs closer to the middle of the room so that they could see me get spanked.

"Put your hands over your head and keep them there." Jane said to me. It felt like I had a hundred eyes on me as Jane unbuckled my belt, unzipped my zipper, and pulled my pants down to my ankles. Next I felt her fingertips in the waist of my boxer shorts.

My hands came down to stop her and I said, "Can't you leave these on. I don't want to be spanked on the bare in front of all these women."

"Put your hands back over your head!" Jane commanded me. "You know I always spank you on the bare." Soon my boxer shorts were at my ankles and Jane had me step out of them. I was now standing naked from the waist down in front of all of these women. I had an erection with everyone starring at me, like this.

The women started to whisper to each other as Jane said, "You can now bring your arms down from over your head and bend over my lap for your spanking." To make my embarrassment even worst, she said, "Now spread your legs so that I can give you’re a through spanking."

I didn't want to spread my legs because then everyone could see my penis and balls hanging down and Jane could spank me in the tenderest parts of my bottom. But I spread them, anyway, because I knew that I could expect an even harder spanking if I didn't spread them.

One woman came up and handed Jane one of the paddles and said, "Why don't you start his spanking with this paddle?"

"Sure, this looks like a well made paddle. Let's see how well it works." Jane said. Then my spanking started.

SPANK, SPANK, SPANK.

After a few well placed hard spanks, I forgot about the other women in the room and just thought about the spanking that I was getting. Jane was spanking me harder than she usual, and I was moaning and moving about while I was being spanked. Other women came up and handed Jane different spanking implements to be used on me. My poor bottom was now feeling very warm.

SPANK, SPANK, SPANK.

"Clyde's bottom looks red and well spanked," Jane said. "I am going to stop spanking him, now. If any of you would like to spank Clyde, please line up and sit down here to spank Clyde. The rest of us will now have refreshments and talk to each other. You can stand up, now."

I stood up and rubbed my poor sore bottom. Then three women came up to where Jane had been seated. One young woman sat on the chair and said, "Hello, Clyde. My name is Amy, and I am Jane's niece from Nebraska. I have never spanked a man before, so this should be interesting. Please bend over my lap for your spanking." Amy hiked up her skirt and I went over her lap. I still had an erection and my penis went between her legs. I felt so embarrassed being spanked by a woman half my age.

"I see that your bottom is already a nice red shade." I felt her hands all over my upturned bottom. "So I won't spank you very long, but first I want to feel your body." I next felt her hands going up and down my back and then I felt her hands on my upper thighs. I began to move about because of her exploring hands. "Stay still." She commanded me. Then I felt her hands between my legs and I felt her hands on my penis and balls. "Now your spanking will begin," Amy said.

SPANK, SPANK, SPANK.

My poor bottom was already sore from Jane's spanking, so I moved about a bit. Amy just grabbed a hold of my waist and held me tighter to her body while she spanked me.

SPANK, SPANK, SPANK.

After a few minutes Amy said, "Yes, I see where you will make a good husband for Jane. Stand up, now, and let the next person spank you."

Then the next strange woman sat down, told me her name, and spanked me. By the time the last woman was done spanking me, my bottom was very sore and red.

I yelled out to Jane, "Is it okay if I get dressed now? There is no one else to spank me."

Jane asked the group of women, "Does anyone else want to spank Clyde?" No one answered, so she said, "I guess you can get dressed. Then mingle with my friends and family. I'm sure they will all want to talk to you and meet you."

So I got dressed and got some refreshments. Most of the questions I got were of the spanking nature. How long has Jane been spanking me? Do I enjoy being spanked? They asked me a lot of questions like those. Her friends and family were very nice and friendly to me.

After everyone had left, Jane said, "I'm very proud of you allowing me to spank you in front of all my friends and family. But that is one of the reasons that I am marrying you!"

I wondered what her family and friends were going to think of me as I got married in the church. Would their thoughts go back to seeing me spanked at Jane's shower?
 

My Date - Part 21 - Bachelor's Party

Jane just had her wedding shower, and she invited me to it. To my surprise, they gave her a lot of spanking implements as gifts, and I was spanked in front of all of her friends and family. But now it was my turn to have a Bachelor's party. I invited Jane to my party to meet my friends and family. My party was a lot smaller than Jane's party. It was held in the basement of a bowling alley. Those attending my party were my brother, Charles from Chicago, he is also my best man; my best friend Tim, and my father, Bob. All of us sat around a small table and we were drinking beers. Somehow the conversation turned the spanking I had received at Jane's shower.

"Yes, I spanked Clyde in front of all of my family and women friends." Jane said. "When Clyde proposed to be, he agreed to be spanked by me or my friends at any time or at any place. And that's what happened to him."

"Well don't you think what is good for the goose is good for the gander." Tim said.

"You have spanked Jane, before? Haven't you?" Charles asked.

"Several times. But never in front of anybody." I replied.

"Well I think you should spank Jane right now." My dad said. "This will show her that you are also in control of the household."

"But I don't want to be spanked!" Jane exclaimed.

"Either you submit to a spanking, or we will help Clyde spank you." Tim said.

"Clyde submitted to a spanking in front of my guests, I guess I can submit to a spanking in front of his guests. How do you want me?" Jane asked.

My dad pulled out a chair and placed it in an open area in the room. "Clyde, you sit here and spank Jane. Jane, go over to Clyde for your spanking." My dad said.

"I'll find something to spank her with!" Said Tim as he ran out the room.

Jane had on a nice short dress on. "Hold your arms up so that he can take off your dress," Charles said. Jane's arms went up and soon she was standing before me in just her bra and panties.

"I'll hold her arms up while you slip down her panties." Charles said.

"Can't I leave on my panties?" Jane pleaded. "They don't give me much protection, anyway."

It was true; they were very skimpy bikini panties. But since I was spanked on the bare I said, "You spanked me on the bare, so you will be spanked on the bare, also." Then I slowly pulled down her panties, and took off her high heel shoes as she stepped out of her panties. Before us was Jane, standing with Charles still holding her arms above her head, with only her bra on.

"Please spank me and get this over with." Jane said. "It is so embarrassing being exposed like this!"

"See, now Jane is begging you to spank her!" My father said.

"Charles, let go of her arms and now Jane you can lay over my lap for your spanking," I said.

Now her nice, upturned bottom was over my lap. It was nice to be the one doing the spanking instead of the one being spanked. I first ran my hands over her soft, white bottom. Jane squirmed a bit and said, "Don't play with my bottom, just spank it!" Then her spanking started.

SPANK, SPANK, SPANK.

"It is so good to see a woman spanked, especially right before she is married." My father said.

SPANK, SPANK, SPANK.

"You have chosen a lovely wife." Charles said. "And she has a lovely ass!"

SPANK, SPANK, SPANK.

"I think she is beautiful, even when she is being spanked." I said.

SPANK, SPANK, SPANK.

Then Tim ran into the room carrying a ruler. "This is the only thing I could find to spank her with. I hope it works well." Then Tim handed me the ruler. He looked down at Jane and said, "You sure are getting a good looking wife."

"Thank you!" I said. Then I started to spank Jane with the ruler. WHACK!

"Ouch! That hurts!" Jane exclaimed.

"It's only a ruler. You have used worst things on me than a ruler." I replied. It did leave a nice red spot on her bottom.

WHACK! This time Jane's hands came up to protect her bottom from the sting on the ruler. Charles immediately came over and held her arms so she could not protect her bottom from the ruler.

WHACK! "Do you have to spank me with that?" Jane pleaded.

WHACK! This time Jane started to kick her legs. "I'll come over and hold her feet in place." Tim said.

"When you hold her feet, spread them apart a bit. She always wants my legs spread when she spanks me." I said.

"Please don't have him hold my legs like that." Jane pleaded. "It is bad enough being spanked in front of them, but it is just awful for him to hold my legs like that."

WHACK! "Be quiet, or else your spanking will even last longer!" I said.

WHACK! WHACK! WHACK! Her bottom cheeks were now turning a nice pink color and Jane was squirming about.

WHACK! "Does anyone else want to spank her?" I asked.

At this point Jane was almost crying when she said, "Please don't let anyone else spank me."

"You let your friends and family spank me, so now you will see what it feels like. Now stand up!" I ordered her.

Tim quickly sat down where I had been sitting. "Jane, bend over my lap so that I may spank you."

Jane lay over his lap and her spanking began again. We started to grab her arms and legs and Jane cried, out. "Please don't hold me in place. I'll be a good girl and stay in place for my spanking>"

Then Tim started to spank Jane with the ruler. WHACK! WHACK! WHACK! Jane was being real good and she kept her hands away from her nice pink bottom.

WHACK! WHACK! WHACK! "You can stand up, Jane. Does anyone else want to spank her." Jane rubbed her bottom as Charles seated himself.

"Over you go again." Charles said. As he rubbed her bottom, he said, "Her ass is also getting nice and warm. Jane will make a nice wife for you!" Then he proceeded to spank her with the ruler.

WHACK! WHACK! WHACK! "I better let Clyde's dad spank you, before you can't take any more. Stand up, Jane, so that Clyde's dad can spank you."

Jane was almost in tears when Charles got out of the chair and my dad sat down. "Please ask me to spank you." My dad said to Jane.

"Please spank me, Sir." Jane replied.

"I'd be happy to. Now get your sweet little ass over my lap." My dad said.

WHACK! WHACK! WHACK! Then he started to spank her with the ruler. WHACK! WHACK! WHACK!

"I think Jane has had enough!" I said. Jane's poor bottom was now a bright red. "Please stop, Dad."

My dad helped Jane into a standing position and then she ran over to me. We embraced and she cried a little bit. "Now I really know what it is like for you to submit to spankings from me and my friends. You have been really good about accepting being spanked. My spanking, today, should really help our relationship."

"I better go now with Jane." I said to the group. Jane slipped on her dress, but didn't even attempt to put on her panties over her sore bottom. She just threw them into her purse and I drove her home. We actually had a wonderful lovemaking session that night. Tomorrow is our wedding. I guess both of us will now be walking down the isle with sore, red bottoms.


My Date - Part 22 - Wedding Night

Well, the blessed event finally happened. Jane and I are now married. The wedding ceremony went well, and we had a good reception. Although both of us walked down the aisle with hurting bottoms from our recent spankings, with had a passionate kiss at the end of the wedding ceremony.

The family provided us with a limo to take us to one of the nicest hotels in town. We got the honeymoon suite, which had a large king size bed, a sofa and chairs, and a bottle of champagne. The next morning we would be flying out to Hawaii, to spend our one-week honeymoon.

I am so glad that I am now married to Jane. Not only is she a beautiful woman, but I like how we think alike, value the same things in life, and are so compatible. Jane has been the only woman who has understood my sometimes crazy behavior, and loves me just as I am.

Although I was a bit surprised when Jane first spanked me, I now feel that it is her way of letting me know she loves me. It also puts us in intimate physical contact, which I enjoy. I don't enjoy having a sore bottom for a couple of days after my spanking, but the spankings show that she really cares about me.

I have also spanked her a few times. I think after her last spanking that she has a better understanding how I feel when Jane or her friends spank me. My spankings have shown me that I need to totally respect Jane and other women. I had never met a self-confident woman until I had met Jane. This is why I have agreed to be spanked by Jane anytime, and anyplace. My spankings help me to always remember to respect women.

Jane and I had a wonderful dinner at the hotel, then we went up to the room for some champagne. After each of us had a glass of champagne, Jane said, "Wait out here while I get ready for bed. I have a surprise for you!"

So I waited outside of the bedroom while Jane got ready. Jane can be very creative at times, so I didn't know what to expect. When she finally opened the door, Jane was wearing a very flimsy and revealing red nightgown. She took me by the hand and led me into the bedroom. On the bed were three paddles. One was wooden and had holes in it. One was a leather paddle, and the last one was like a ping-pong paddle.

Jane sat down on the bed and said, "Before we consummate this marriage, I want to spank you. Please put your hands above your head so that I may prepare you for your spanking." Then Jane slowly took off my tuxedo, slacks, underwear, and even my shoes. After she put two pillows in the center of the bed, she said, "Please lay on the bed so that your bottom is raised high by the pillows." Once I was in this position, she got out wrist cuffs and secured my wrists to the bedposts. "Spread your legs." Then she secured my legs to the bedposts. Now I was spread-eagled on the bed, with my bottom raised by the pillows. "You will get 25 swats from each paddle. Please count them out loud."

I always hated counting out the swats of the paddle. It made me acutely aware of each swat that I would receive. Then my spanking started. Jane started with the paddle that was like a ping-pong paddle. It didn't hurt too badly, but it did warm up my upturned bare bottom. Next came the leather paddle. This paddle did sting me a lot more. I was still able to count aloud the 25 swats.

Then came the wooden paddle with holes in it. This paddle really stings my bottom. After only five swats, I was squirming about, but was unable to move very much because I was secured spread-eagled on the bed. "Stop moving about or else you will receive 30 swats from this paddle," Jane said.

It took all it had in me from moving about, but Jane delivered the 25 swats to my poor upturned bottom. Then I saw her reach over to the nightstand next to the bed and grab a jar. I next felt soothing cold cream on my burning bottom cheeks. Usually Jane has never rubbed anything on my bottom cheeks after a spanking, so this was a pleasant surprise for me.

Jane then kissed me and was releasing me from the bedposts as she said, "I love you, Clyde, and I look forward to spanking you many more times."

I sat up on the bed, and then to Jane's surprise, I forced her over my lap. She was wearing very thin red panties that matched her red nightgown. I quickly slid her panties down, grabbed the leather paddle and began to spank her.

"What are you doing?" Jane asked.

"I know that I have agreed to be spanked by you during our marriage, but I also want you to know that you will be spanked by me when I feel that you have been naughty." I said. I kept spanking her as we talked. It was nice to see her bare bottom turn red for a change.

"But I didn't agree to be spanked before we got married. You were the only one who agreed to be spanked by me at any time and at any place." Jane said.

"But since we are now married, this is how it will be unless you want a divorce." I said.

"No, I don't want a divorce." Jane said. "But I want to make it clear that I will do most of the spanking. Ouch! Is that understood? Ouch! Ouch!"

"You are in no position to made demands." I said as I kept spanking her. "But yes, I will honor our agreement and will be willing to be spanked by you at anytime and any place."

Then I reached over and grabbed the jar of cold cream. I grently spread it over her nice soft, but red bottom cheeks. Jane purred as I rubbed the cold cream into her warm bottom. My fingers wandered between her legs and felt her warm moist sex.

"Let me up so that we can make love." Jane said.

So I let her up, Jane took off her nightgown, and we made passionate love into the night. I am looking forward to a wonderful marriage with Jane.

End

This is the end of this series called "My Date". If there is another series I guess it could be called "Jane" or "My Wife". I am sure that I will continue to be spanked for many years to come. Clyde.