High School Reunion Part 07 The lotion felt good and it really helped that I was able to get off the bench. While we were moving the bench several women thanked Sally and me for the opportunity it gave the women to finally pay me back for the suffering that I caused them. Then I had to mount the spanking bench again and be secured to it. During the second round I could feel the heat build up in my lower regions and now I was feeling the strange sensation of both pain and pleasure at the same time. I was also more acutely aware of each woman's perfume and unique female scent. Since had already known Ann and Sally, I was now able to remember their names. It was still embarrassing and painful for me, but this second round was easier to endure. When it was Sally's turn to spank me she announced to the group, "Since no one has used the cane on Clyde yet, I will now administer `Six of the Best'. If you want to, you can gather closer to watch this. The cane really hurts more than you can image and will leave small ridges and red welts on his bottom. Clyde, will you count the strokes out loud for the group?" Since Sally likes me to address her as `Mistress' when I am being spanked by her, I replied with "Yes, Mistress." Some of the women giggled and Sally said, "I have taught Clyde to answer me that way when I spank him and because it shows me more respect." I felt the cane tap my bottom a few times, heard the whistle of the cane and then it felt like many bees had stung me in a straight line on my bottom. "One. Thank you, Mistress." Sally paused a while and said, "See the thin red welt that is forming in a straight line on his bottom." I heard the women whisper to each other but I couldn't hear what they were saying. Then I felt the tapping again, heard the whistle and felt the pain of fire again. "Two, Thank you, Mistress." By the time the sixth stroke landed there were tears in my eyes and I could barely say, "Six. Thank you, Mistress." "Now we will break for a light lunch and you can look at and fell Clyde's well-spanked bottom before you leave the room. We will get back together again in about an hour," Sally told the group. I could feel many hands on my poor bottom and Sally rubbed some more lotion on me. "I will leave you secured to the bench while I grab a quick lunch and I will bring you back some water and something to eat," Sally said to me. You are taking this very well without complaining. When she finally came back, she released me from the bench and had a glass of water to drink and a small salad to eat. Then she had me move over a large armless chair and a smaller lower chair. Sally placed them in front of the spanking bench so they were facing each other. She next got the pillow and towel from her car and placed it on the seat of the smaller chair. "That will be the chair you will be sitting on." She also had a woman bring out some tissues and several hand towels and bath towels. Then Sally gathered all of the women in the room again and told them, "This will now be the part where you will have one to one time with Clyde. Each of you will have fifteen minutes to spend with him, and use the time however you want. If you want to spank him some more, you can either give him and over the knee spanking or he will mount the spanking bench for you but I will not secure him to it. Since Clyde has been spanked so much already, if you use the spanking bench, please limit your spanking to less than three minutes. If you give him an over the knee spanking with your hand, you can spend the entire time spanking him that way. I do hope you tell him how his playful practical joke has affected your life in many ways for many years. There are tissues available if you and/or Clyde get emotional and cry. There are also towels available if you don't want to possibly mess up your clothes while giving him an over the knee spanking. You can either sit in the big chair or stand while Clyde sits in the smaller chair. I want everyone else to leave the room so this will be your private time with Clyde. I will occasionally stop in to tell you about the time that is left and to make sure everything is okay. After your fifteen minutes of private time you can either leave or stay for a brief wrap-up session. Ann, you will start first and everyone else should clear the room." Ann was one of the women I picked on a lot because I liked how she reacted to what I did to her. She would usually scream out loud and cause a big scene to happen. I was surprised how my pranks influenced her dating life and her marriage. She had and still has a hard time trusting men because she believes all men will try to embarrass her or humiliate her. It really hurt me to hear her tell me these things and I asked her, "Would it help if I mounted the spanking bench so you can spank me some more?" I was surprised that I said that to her because my bottom was very sore and hurting from my previous spankings. "Yes, it would help me a lot if you would so I can get rid of my frustrations by spanking you some more." Ann grabbed the paddle I hated the most, the large wooden paddle with holes in it and started spanking me. It did really hurt but didn't hurt me as much as the suffering I caused her. At the end of my fifteen minutes with Ann, she did thank me for allowing me to hear her story and to be able to spank me. It did make me very sad that I had caused all of this painful emotional and physical hurt for these women. Most of them, at some point, gave me an over the knee hand spanking. This way I could feel their emotional pain even more because of their breathing and the way they spanked me. I also felt closer to them because I could also feel their body heat and smell their special scent. Although my bottom was really hurting, I gladly mounted the spanking bench for them so they could spank me some more. After my one to one time with all of the women including Sally, all of the women gathered in the room again. Sally had me sit on the small chair in front of them, with my hands fastened together behind my back and my knees wide apart. They discussed how helpful this gathering was to them and they appreciated all of the hard work Sally had put into this and that she had worked with me so that I was willing to be spanked by them and listen to their stories. Sally helped me stand up and then I apologized to the group again. The Sally said, "I also want to thank the XXX store for allowing us to use one of their spanking benches. You can leave now but I want to demonstrate something the XXX store sells and embarrass Clyde one more time." "I need you on the spanking bench one last time and this time I will secure you to it." Sally secured me to it and made sure the straps around my upper thighs were very tight. "This is called a prostate massager, but this one has a vibrator and works with a wireless remote control." I was embarrassed as she lubed my bottom hole and guided it into me. Then she had Ann put a condom on my penis and had the women gather close around me to watch. "There are five different modes and you can control the intensity in each mode. I will use the pumping mode at medium intensity for Clyde and watch what happens." I could feel my cum dribble out of my penis into the condom. They were amazed that I was being milked this way without anyone touching me. As the women left the room many of them commented how bright red my bottom was and about the six parallel welts that could be clearly seen from when Sally used the cane on me. To add even more embarrassment for me, Ann reached down and pulled the condom off my penis while I was secured to the spanking bench. Then she used a hand towel to clean me up and said, "I am going to keep this as a reminder for me of what took place with you." Eventually Sally rubbed some cooling lotion on me and released me from the spanking bench. I told her, "Thank you, Mistress." "Clyde, I think you got what you deserved and now you have felt some of the pain that you put the women thru. I hope this experience will make you a better man. Now let us get you ready for your ride to my house." Now I was finally able to put back on my lounge pants and t-shirt. Then Sally connected my wrist cuffs together in front of me and attached them to my collar. She escorted me through the house and I sat down in the car on a pillow with a towel on top of it. The seat belt was fastened, a blindfold was put on me, and I was now in the back seat next to Ann again. Soon we were traveling down the country roads again and first we dropped off Ann and then Mary. I was so relieved when I finally heard a garage door open, we drove in, the car was shut off and the garage door was shut. My blindfold was taken off, my wrist cuffs were unfastened and I went into Sally's house. Sally brought in my duffle bag from her trunk of her car and said, "There is something I want to show you before you leave. Come over here to what looks like a large desk and help me with it." The desk was fake and only a thin wooden shell. When we moved it away, there was a spanking bench behind it. "Becky put wheels on it so it is easy to move it anywhere I want it. Help me move it to the middle of the living room." I did so and then Sally showed me the lever that made the wheels retracted and it was resting on her carpet. Take off your t-shirt and lounge pants so that I can secure you to it." This was not what I had anticipated once we arrived at Sally's house. This bench was like the other one that had added straps so that my thighs were held as far apart as possible. While I was helplessly secured to the bench Sally said, "I have grown close to you and I enjoy being with you but now I feel you know how to give women the proper respect. You have felt the hurt you have caused women with your practical jokes and pranks you have pulled on them. Do not answer me today, but if you decide that you still want to have a relationship with me, you will be spanked and you will need to keep yourself well shaven. Also, if I hear from other women that you embarrassed and humiliated, that I will allow them to spank you and tell you their stories." "Yes, Mistress," I replied. "I am going to give you one last light spanking before you go, and then you will help me put the spanking bench back where it was. Then call me or email me if you want to get together again. As I said, I didn't think I would like a jerk like you but you have changed and I have grown to like you." Then she used one of my paddles and gave me a light spanking. It still hurt a lot because I was still red and sore from my previous spankings. After she released me from the spanking bench she said, "Do not say a word or talk to me. Help me put back the spanking bench, change back into you regular clothes, put everything back into your duffle bag and leave my house. I want to hear from you sometime on Sunday as to what your decision will be." So I did so and left Sally's house without saying a word. My bottom and my feelings were hurt by what took place today. I knew that I would be sleeping on my stomach and figuring out if I wanted to continue seeing Sally.