My Journey to Submission Pt. 04

This is the fourth part of my journey. You should read the first three parts to understand the people and how we got to this part of my journey.

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I kept thinking about again being with Karen's Mom. I yearned to once again feel her power and strength. I yearned to take the pain for her. I needed to please her and then be allowed to pleasure her. Every time we've been together I felt myself becoming closer to her and more accepting of continuing my journey of submission to this spectacular older woman.

It was in the late 1970s in a midwestern university town. I was in my senior year and getting close to graduation. It had been almost two weeks since I was last with Karen's mom and then heard the news about Karen. I finally got the phone call. Karen's mom told me to be at her home the next night at 8pm. She said this will be an especially memorable time together. I cancelled my plans and counted the hours until when I could be with her.

I knocked on her door promptly at the designated time. Karen's mom answered and looked lovely. She was in her late forties. Her beautiful face and curvy body once again caused my cock to swell. She invited me in and Karen was still not there. I looked over to the couch and noticed someone else was there. I could see the outline of silver hair. Karen told me to strip and to then present myself in front of the couch. She went to the couch and sat down.

When I got to the couch I first noticed the stern look from an elderly woman. She had to have been in her sixties or maybe seventies. She had short silver hair which was styled in a permanent wave. She appeared to be tall and lean. She wore a fancy dress that went past her knees with black nylons underneath. I noticed she wore a large pearl necklace and some other expensive jewelry. Karen's mom told me that this was her dearest friend, Lady Elena. Lady Elena was very special to her and I was to treat her commands exactly as if they came from her. She then told me not to embarrass her. She then said to Lady Elena that I was becoming a dear toy boy to her.

Lady Elena glared at me and said that Karen's mom had spoken highly of me but that the proof was in the pudding. I wasn't sure what that expression really meant but I took it to mean that I better do as I was trained. Karen's mom then said to Lady Elena that I was recently trained to be her piss slut. She also mentioned that I was trained to take her thick ten inch cock deep in my ass. She said I had excellent oral skills and took a hard spanking. Lady Elena said she wanted to also enjoy how I could take a hard spanking.

They rose and Karen's mom grabbed my cock and balls and led me into the kitchen. The kitchen table had been cleared off and positioned in the center of the room. Karen's mom ordered me to lie across the table on my stomach. She told me to place my arms in front of the table and she tied each wrist tightly to the table legs. There was no padding on the table. I felt the hard wood pressing against my cock, balls, hips, chest and elbows. The chairs were pushed away and they positioned themselves across from each other on both sides of the table.

Lady Elena said that she had taught Karen's mom that sessions started with a hard spanking to put the boy in his right place. The spanking should bring the boy to tears so that he would demonstrate that he would take the pain for his Mistress and know that his place was to serve her. Karen's mom began by spanking my ass with her right hand. As soon as she lifted her right hand then Lady Elena spanked me with her left hand. They continued to alternate hard spanks. I felt that I never have had such a hard spanking. It only took a few hits for me to start begging and crying. The combination of the alternate hits and pressing my body into the unforgiving wooden table made this especially painful. This continued for a long time and they seemed to become even more aroused by my begging and crying.

They finally stopped. Karen's mom rubbed my red ass and Lady Elena commented that I did well to take their spanking. Karens' mom untied my arms and helped me off the table. She told me to stand there while they each refilled their wine glasses and had a private conversation.

Karen's mom then told me how Lady Elena was the woman who introduced her to the world of domination. Lady Elena mentioned that they shared a passion and took it out on her poor husband Bob. Karen's mom said that they have a wonderful time together and that she was so appreciative of the difference Lady Elena made in her life. She told me that Lady Elena is a true sadist and that she wanted me trained by her to accept more pain. She told me again that I could leave at any time but that if I left now that I would never see her again. She asked if I wanted to leave now. I said that I needed to continue my training and that I will take the pain for her. Karens' mom smiled and that sent shivers through me.

They finished their wine and Karen's mom grabbed my cock and then led me into her large master bathroom. Lady Elena said how she wants her boys to be clean shaven. She produced a razor and shaving cream from a large black bag. Karen's mom grabbed the tip of my cock and Lady Elena lathered it with shaving cream. She then very expertly shaved my cock and balls. It was somehow tender and stimulating. I became even more aroused. Karen's mom then told me how I was to soon experience the joys of cock and ball torture. I was concerned but trusted Karen's mom.

Lady Elena commented that Karen's mom should really get the right bondage equipment but that she knew how to properly display me. She led me to the solid door between the bedroom and the living room. She had me stand with my back to the door. She tied one rope to each wrist. She threw the rope over the door hinge and the woman passed it back and forth through the crack to secure the rope to both hinges. The other rope was first tied to a large clothing hook placed on the top of the door and then tied to the door knob. I was securely fastened to the door by my arms.

Lady Elena then reached into her bag and put on a black glove. She gave me a look and then grabbed my cock with the glove. I immediately felt all the sharp points from the glove. She twisted the glove around my cock as I moaned and begged her to stop. She asked me if I wanted her to masturbate me with her studded glove. I said no, please no. Her intense look gave me the shivers.

She finally released my cock and took off her glove as she reached once again into her black bag. She pulled out two clamps. She told me that it was now time for nipple torture. I never had my nipples tortured so I was not sure what would happen. I soon found out. Lady Elena grabbed one nipple and started to twist it hard. I cried out and caught Karen's mom look of arousal which helped me through the pain. Lady Elena attached the clamp and I felt the surge of pain which caused me to shake. Lady Elena looked satisfied and stood back to watch my discomfort. She then twisted my other nipple and attached the second clamp. I shuddered even harder. Karen's mom came to me and told me to breathe through it. She said Lady Elena was an expert and no permanent harm would be caused. She said she was so proud of how I was taking the pain for them.

Lady Elena stepped back and reached into her bag once again. She removed a short nylon rope and tied it around the base of my cock. She used the rope to separate my balls and tied the rope tightly around my cock with only the tip showing. She removed several wooden clothes pins from her black bag. She carefully placed the wooden pins on the very tip of my cock. Each pin caused me to shake with pain. Karen's mom placed her lips next to mine and kissed me deeply. She told me once again how well I was doing. Lady Elena stepped back and admired her work. She looked at me intensely but did not smile. I never saw her smile. Her intense look was one of satisfaction and arousal.

She reached in her bag one last time. She brought out a small device with a sharp wheel at the end. Her eyes got even more intense. She took a deep breath and strode up to me. She carefully rolled the wheeled device on the small amount of my cock not covered by rope or pins. The feeling was so intense. I banged my back against the door and cried out. She then placed the sharp points on my exposed balls and ran the wheel all over them. I almost completely melted down. Karen's mom saw this and told Lady Elena that I had demonstrated my devotion. Lady Elena stepped back and appeared satisfied.

It hurt like hell when they removed the clamps (they hurt the most), the pins and the rope. I was spent but satisfied in knowing I had done well for Karen's mom. They untied the ropes from the door and led me to the foot of the bed. They stepped away and had a private conversation. Karen's mom then came next to me and told me to do all that Lady Elena commanded and that she may reward me later if I do well. She then left and closed the bedroom door behind her.

Lady Elena gracefully removed her jewelry and then dress. She gave me an intense look. She had extensive hair covering her pussy. Karen had shaved her pussy and Karen's mom had only a little hair so this was different for me. She positioned herself at the top of the bed and placed her hands behind her head on the pillow. She told me to crawl to her and display the oral skills taught to me by Karens' mom.

I knew I had to perform well and I did. I licked her pussy exactly as I was taught. I used long licks from the the bottom to the top of her slit and make these increasingly deep. As I felt her respond then I began to caress her clit. I looked up and her expression had not changed. She seemed passive and did not make any noise or change her stern look. I did feel some of her juices flowing and continued as I was taught. I licked even longer when I thought the time was right because Karen's mom taught me that it always took longer for the lady then the boy thought. I did eventually began to kiss her clit with more force. I felt Lady Elena respond and there was soon a small discharge. I continued to lick as I was taught but Lady Elena pushed my head away. She said I did an excellent job and that she was very pleased. She told me to continue to lay in this position until Karen's mom told me to do otherwise. She then got up and went into the bathroom. A few minutes later I heard her leave the room.

I eventually heard the front door close and soon Karen's mom came into the room. She walked past me. She smiled and removed all her clothes. She positoned herself at the top of the bed and told me to do what I do so well. I immediately caressed her beautiful pussy. I loved the way she tasted and how she responded when my tongue was deep in her pussy. She thrashed and moaned and told me that I was doing another wonderful job. She came several times and I continued to pleasure her through it all. She then caressed the top of my head and gently moved my head to one side.

She told me that she knew I thought licking her pussy was a reward and that it is. However she said that I had done such a wonderful job tonight that she thought I deserved even more reward. She got up and told me to lay where she was. She then crawled on top of me and placed her bottom on my chest. She moved her lips to mine and kissed me deeply. I kept my hands at my side although I wanted to hold her even closer. Karen's mom then broke our kiss and moved her body further down my body. She lifted herself up and grabbed my cock and placed it deep into her wet pussy. It was heaven. It was our first time being together this way. She moved up and down on my cock as I laid there. I enjoyed every moment. When I came, I came so completely that I really lost track of where I was. It was bliss.

Karen then rose off of me and again kissed me deeply. She told me that she wanted me to spend the night. It was the first time I was asked to stay over. I was thrilled in so many ways.

TO BE CONTINUED