Grocery Store Part 19 Now it is Wednesday, and when I was attending classes, all I could think about is the spanking I was about to receive from Mrs. A. I felt that I didn't need to be spanked, but Mrs. A felt my spanking was needed since I was still not keeping the house clean and I had neglected her by going to the cabin with Liz and Mary. I was anticipating having a nice supper with Mrs. A, then taken to the punishment room for my spanking. To my surprise, when I arrived at Mrs. A's house, Jane was in the kitchen. Jane is a co-worker of Mrs. A, and she got to see me and feel me in my panties on Monday morning. What was even more embarrassing for me was that Jane appeared to be only a few years older me. "Clyde, I am glad you arrived home." Jane said. "You have good timing, supper is almost ready to eat. Go change into your panties and t-shirt while I finish up with the food." I never expected that Jane would be at Mrs. A's house. But I went to my room and changed into just my little pink panties and t-shirt. When I entered the kitchen, the table was set and the food was ready to be eaten. Jane was already seated and she said, "Before we eat, I want to have you stand by me so I can feel you in your pretty panties." So I stood by her, with my hands on my head, and I became excited as she felt me through the thin material of the panties. "I like the way you react to my touch. But sit down and let's eat. Then I'll explain to you what will take place this evening." The food tasted really good. It was fried chicken, mashed potatoes, and green beans. Jane even had fixed a nice salad and there was a piece of apple pie for dessert. "Joyce, Mrs. A to you, had an important meeting that she needed to attend at the last minute. She had most of the food cooked already, so she invited me over to eat with you and spank you. Before she left, she gave me the key to the punishment room and showed me a few things about it. Joyce told me that you were very cooperative in being spanked, and she wants you to show me this same cooperation. I am supposed to call her before she arrives home. If she hears you did not submit and cooperate with me, Joyce will spank you again. Any questions?" I knew I was going to be spanked, but I didn't expect to be spanked by Jane, who I had just briefly met. "No Mistress. This is a surprise for me. But if I need to be spanked by you, I will cooperate." I said. "It is nice to hear you address me as Mistress." Jane said. "Mrs. A wants me to address all women that as Mistress, from now on." I replied. "That is a nice touch. Women will like it when you address them as `Mistress', and they will sense that you are submissive to them. I used to spank and still spank my younger brother. So when Joyce told me about you, I wanted to meet you and possibly spank you. So I am happy that she had this last minute meeting. Joyce also told me that you would show me which paddles to use on you, and you would position yourself on the spanking furniture. Is that correct?" "Yes Mistress. I guess I will do that for you." I reluctantly said. "She said that she wanted me to end with a prostate massage vibrator. That you would know where she kept it and that you would help me with it. I guess it relieves you of all of your sexual tension at the end of your spanking. Is that true?" When that is used on me, my cum seems to just dribble out of me, so I wasn't looking forward to the prostate massager. But I answered with, "Yes Mistress, I can help you with that too." "Good! Lets finish eating and I will quickly put the leftovers away. We can clean the dishes after your spanking." So I took my time eating because I wasn't looking forward to be spanked by Jane. When she saw that I was finished eating she said, "Go to the bathroom and then head downstairs. I will be there shortly. Joyce told me that you were to stand outside of the punishment room in only your panties and slippers. So leave your t-shirt up here." I washed up, left my t-shirt on my bed, and went downstairs. Whenever I stand outside of the punishment room, I am always suppose to stand with my legs apart and my hands on my head. So I stood like that, waiting for Jane to finish up and spank me. When Jane came down the stairs, I was surprised to see that she had taken off her dress and she was dressed in only her bra, shoes, and panties. Jane had a very nice slim body, and now I could clearly see that she had nice full breasts. She also must of put on some more perfume, because she smelled really good. Between smelling her perfume and seeing her in only her bra and panties, this made a tent in my panties and I became very excited. "Joyce told me you have a girlfriend named Liz that likes to warm you up with an over the knee spanking before you are spanked in the punishment room. I that true?" "Yes, Mistress. It makes it easier on me if I am going to receive a more severe spanking." I answered. "It sounds like a good idea to me." Jane said. "Tell me more." "Liz sits on the couch so my full weight is not on her, and my penis goes between her thighs." "Okay. Let me first spank you that way. It sounds like I will get to know you a lot better." So Jane went over and sat on the couch. "Stand by me so that I can pull down your panties." So I stood by her with my hands on my head while she slowly pulled my panties down to my ankles. I stepped out of them and Jane put them aside. "I like the way you keep yourself so well shaved." Jane said. "It makes you look like a naughty little boy." Jane spread apart her thighs and said, "Now lay over my lap." Then I felt her thighs close together and I was held in place. I felt so embarrassed being spanked like this, by a woman just a few years older than myself and I had just met her. Jane didn't spank me very hard but she liked to caress my naked upturned bottom between spanks. Also, when she spanked me, her fingers wrapped around so that I was spanked in my most sensitive areas of my inner upper thighs. But her perfume smelled very good, her body felt nice and warm, so I was kept excited as she spanked me. Soon, she had me stand up and she handed me the keys and said, "I can see you can't wait to be spanked, so open the door for me." As I unlocked the door, I felt her fingers on my freshly spanked warm bottom. It felt awkward having to unlock the room where I was about to receive a more severe spanking from Jane. "Please show me where everything is so that I can give you a good spanking." Jane said. So I opened the drawers and pointed out the cuffs and other stuff she needed to spank me with. "Mistress, I can remain still while you spank me, so I hope you won't need to restrain me very much." I told Jane. "Joyce told me you were very good in receiving your spanking. Now where is that prostate massager that Joyce told me about?" She asked. I opened another drawer and handed it to her. "Women like to use it on me at the very end of my spanking, that way I get totally milked." Then I showed her the various spanking implements on the wall. Jane liked the fact that there were so many paddles and other implements to choose from. "Okay, I am ready to start your punishment spanking. Joyce will want to inspect you once she arrives home. I need to make sure you will have a very red and sore bottom. So where do you want to start?" I went over to the wooden X on the wall, and stood in front of it with both my arms and legs spread far apart. I held on to the metal rings that my wrist cuffs were usually clipped to. "I will start you off with the small paddles, and then work my way up to the wooden paddle with the holes in it. I guess that one really stings you." Jane said. Then my spanking started again. I was surprised how skillful Jane was at using the small paddles. Not only was she able to spank my entire naked bottom, but also she spanked me in my more tender areas like on my upper thighs and between my legs. At one point she surprised me by spanking me on the insides of my thighs. When I reacted by putting my legs together, she said, "You told me that you were good at standing still. I may have to put cuffs on you." But then, my spanking continued. Next Jane went over to the cabinet of drawers and said, "Clyde, come over here and knell before me." I felt very humble in this position. "Now hold out one arm at a time." Then Jane put wrist cuffs on me. "Stand up, and put your arms behind you." I heard a click and now my arms were secured behind my back. She had me turn around and Jane brought over a step stool. "First put one foot on it, then the other." Jane commanded. So then the ankle cuffs were put on me. I started to take my foot down and Jane said, "I didn't tell you to take your foot down. Now leave it there." Then she went over to the wall and took down a thin riding crop. Next, she was using it to flick my exposed penis and balls. Being totally exposed to Jane and having her play with my penis and balls gave me an instant erection again. "I like the way you react to me." Jane said. "But I need to continue your spanking, so lay over something else so I can turn your bare bottom nice and red." This time I straddled a special wooden horse that had padding on top. It also had places on each side to place my arms and legs. Once I climbed on it, she had me slide back a little bit so my penis and balls hung down and were totally exposed. There were metal "O" rings that she secured my wrist and ankle cuffs to. With my bottom slightly hung over the edge of this and my knees spread wide apart, I felt totally exposed and embarrassed. "Now I am going to use this large wooden paddle on you. The one with the holes in it." Jane said. "Joyce told me this paddle makes your bare bottom turn red very quickly. So lets see what it does to you?" SWAT! I wasn't expecting that paddle to sting so much. I would of moved about, but Jane had secured me to this spanking bench. "Ouch!" I exclaimed. "This is a very effective paddle to use on you. Just that one swat has turned your bottom into a nice pink shade." SWAT! SWAT! The paddle was hitting my most tender parts because I was so exposed. SWAT! SWAT! "I see why Joyce likes to use this paddle on you. She also told me that your girlfriend's friend Mary, made it special for you." SWAT! SWAT! "Yes, when we were up at Mary's cabin last weekend, she gave the paddle to Liz to be used on me. Mary also has two other identical paddles up at the cabin." SWAT! SWAT! I felt her hands on my sore bottom. "Not only is this paddle turning your bottom red, but it also warms you up." SWAT! SWAT! "I think you are red enough for Joyce. Now let's see how you react to that prostate massager." Then I felt Jane use the lubricant on me, and I felt the massager slide deep inside of me. With my whole bottom part of my body feeling very warm, once it started vibrating I felt a funny feeling in my whole body. At the same time, Jane was also applying a cool liquid lotion on my poor sore bottom. Her long fingers continued applying the lotion all over me, and eventually used it on my exposed penis and balls. My body shook and felt totally relaxed as I felt my cum dribble out of my penis. Next, I felt Jane use a tissue to clean up my cum. "I see why Joyce likes to use the prostate massager on you. It really makes you relax and release all of your cum quickly. I also think Joyce will like how red your poor bottom is." Then I felt Jane release me from the wooden horse. I had to put my feet on the stool and she took off my wrist and ankle cuffs. "Now follow me out of this room into the next room and knell down in front of me." Jane sat down on the couch, took off her panties and spread her legs wide. Since I was knelling in front of her, I was directly looking at her shaved pussy. "Have you ever satisfied a woman before?" She asked. "Liz, my girlfriend has had me lick her and suck on her pussy." I said. "Well, I believe after you are spanked and milked by a woman, you should thank her by making her cum with your tongue and mouth. So start by pleasing me now, using only your tongue and mouth." Then I felt her press my head between her legs so that my mouth was right up against her pussy. Jane smelled and tasted a lot different than Liz. I used my tongue to go up and down her pussy, also circling her clit, and eventually my tongue plunged deep inside of her. Jane was moaning and her body was jerking. Soon Jane yelled out, and I felt her wonderful nectar flow out of her and all over my face. But she held my head close to her pussy and said, "Yes, you are very good. Keep going." So I kept sucking and using my tongue on her. Time and time again, I felt her nectar flow on my face. Then I heard Mrs. A's voice coming from in back of me. I tried to turn my head to look at her, but Jane held my head in place. "I see you have done a good job of turning his naughty bottom red and now you have taught Clyde a new skill." Mrs. A said. "Yes, Clyde took his spanking very well. After I used the prostate massager on him, I told Clyde that after a spanking, he needs to thank a woman by satisfying her." Jane said. "I might as well join you on the couch and see how well you trained him." Mrs. A said. Mrs. A took off her panties, hiked up her skirt and said, "Clyde, get your head between my legs and showed me what you have learned." Again, Mrs. A smelled and tasted different than both Jane and Liz. I used my new skills with my mouth and tongue on Mrs. A, and soon I could her moan and move about. Then her unique nectar was also flowing down my face. Her cum shot out with less force, but still soaked my face. "You better clean yourself up in the bathroom while Joyce and I relax on the couch." Jane said. So I cleaned the womanly scent from my face, and further cleaned off my penis and balls. When I walked back into the room Mrs. A. said, "I have asked Jane to come over and help me with your spanking, whenever she wants to. I guess she likes working with you. But go on upstairs and go to bed. It is getting late." So I went upstairs and lay down on my stomach on my bed. Although I had cleaned up, I still had their womanly scent on me and my lower body had a warm glow to it. Soon I drifted off to sleep, with a smile on my face.