6 comments/ 21720 views/ 11 favorites My Journey to Submission Pt. 01 By: davetoyboy I was a 20 year old senior at a large Midwestern university in the 1970s. I was shy and smart and beginning to explore my sexuality. I dated a few women but nothing special had yet developed. There was an older woman who I knew casually during my freshman year. She dated an older guy in my dorm. Her name was Karen. She was tall, slender and had a foxy face with a sharp nose and cheekbones and beautiful light blue eyes. I fantasized about her but did nothing about it. I lost track of her over the years at college. In my senior year, I noticed her in my first class of the semester. She still looked great. She approached me after class and I was so nervous. I was sure I did not made a good impression on her but she did give me a sly smile as she glided away. A few weeks later she approached me after class. She asked me why I was being so shy and said that we should get together. I said sure. She asked me to come to her home for dinner as she and her Mom liked to entertain. We arranged a date and time. I was once again nervous when I arrived. Karen opened the door with a big smile and gave me a peck on the cheek. She introduced me to her Mom. Mom was in her mid forties. She was shorter than Karen and had a few extra pounds. She was curvy in the all the right places and there was something about her. We had a pleasant dinner and then took our wine to the couch. I thought it was interesting when Karen placed me in the middle of the couch with her and her Mom on both sides. Karen cozied up next to me and ran her hand through my hair and to the side of my face. She told me I was nice and that she liked her men shy and obedient. She glanced at my growing hard-on and knew she had me. She told me that she and her Mom were open about relationships. Her Mom smiled slyly at her end of the couch. Karen told me that she liked to take charge. I nodded my head and let her know that that was fine with me. She began to passionately kiss me and then sat on my lap and grinded her breasts and waist into me. When I responded by placing my hands on her back, she pulled away and told me just to let her take charge. She then stood up and told me to get naked. She liked her boys naked. I saw nothing wrong with that and immediately stripped. Karen took my place on the couch and opened her legs wide as she hiked up her skirt. I saw her bald pussy and smelled her excitement. She told me to get down on my knees and worship her pussy. I eagerly did as I was told. I did not have a lot of experience with that but I was eager and enjoyed being so close to her sex. Her Mom watched from her spot on the couch and then asked Karen how I was doing. Karen said I was eager but was only doing average. Her Mom stood up and said that needed to be corrected. She told me to stop and had Karen put her back to the side of the couch She sat back down and told me to lay across them with my mouth at Karen's pussy. I eagerly moved into position. I did not know what was next but this was going just fine and I was revved up. Karen's Mom started to give me instructions. She told me to lift up Karen's ass with my hands and how to caress her slit and clit. When she asked Karen how I was doing and Karen said I was better but not great then her Mom took action. She started spanking my ass with her hand. I stopped and reared back and her Mom told me to lay there and learn or I could leave now and that it would all be over. I did not want to leave. I layed back down and her Mom started gently and then more forcefully spanking my ass. She told me what to do to satisfy Karen's pussy and I had incentive when she said that there would be no enjoyment for me until I showed Karen that I could satisfy her. I did satisfy Karen and she tasted great. I eagerly lapped up her juices and then realized that the spanking did feel erotic. My red ass felt right. Karen Mom's then said it was her turn and I was one again eager to comply. There was definitely something very attractive about her. I felt more attracted to her than to Karen somehow. I did not know why at the time but I do understand it now when I look back. I got on my knees and put all I just learned into practice. Karen's Mom's pussy tasted even better and I thoroughly enjoyed bringing her to her satisfaction. She then rubbed my hair and told me I was a good boy. I realized that I somehow craved her affection. Karen then said that since I did such a good job on both her and her Mom that it was then my time. She told me to stand up in front of the couch. She then sat across from me and took my hard cock in her hand. She toyed with it as she licked my cock and told me that this would be special. I noticed that her Mom had got up and was doing something behind me. It was heaven when Karen took my cock in her mouth. She used her tongue and glided it all around my hard cock. Her warm breath and beautiful face added to the joy. I then felt her Mom came up behind me and she ordered me to spread my legs wide. I did so willingly and she grabbed balls gently and then firmly. I was in heaven with the two women. Karen's Mom began then to spank my ass which only added to my arousal. Karen would pause and play with my cock when she sensed I was getting close to cumming. Her Mom then told me in a strong voice to grab my ass cheeks and spread them. I would do anything at that time to get Karen to finish that blow job. Karen started sucking me again as I felt her Mom's lubbed finger sliding into my ass. I was so focused on Karen's mouth that I just let it all happen. It did all feel so good. I felt Karen's Mom squeeze my balls tightly just before I blew my entire load. I look back now and realize how much more cum I had back then and how thoroughly that feeling of cumming would overcome me. Her Mom continued to finger my ass and squeeze my balls and I continued to cum in Karen's mouth. We then cleaned up and relaxed on the couch. Her Mom said how she hoped this would be the first of many times together. I agreed. I did not know then that this was a start to an intense submissive relationship that would take me on an incredible journey that I am still on today. TO BE CONTINUED My Journey to Submission Pt. 02 This is Part 2 of my story. It is necessary to read Part 1 to set the stage. ***** I couldn't stop thinking about my first encounter with Karen and her Mom. My twenty year old hormones and fantasies kept me thinking about what happened. I thought about the satisfaction from providing oral sex to the ladies, how the spanking and finger in my ass somehow right good and right and I mostly thought about Karen's Mom and how much she turned me on. Karen approached me after class. The first thing she said was to ask me if I had been thinking about our time together. I sheepishly said that I have. With a wicked grin she asked me if I wanted to do it all, and more, again. She knew I was hooked. I stammered that I would but what did she mean by more. She smiled and pecked my cheek and said that I would find out. She told me to be at their home at 8pm on Friday. I went back and forth on whether I was really ready to get more into this relationship. I could not get the sights and smells out of my imagination and of course I went to their home on time. Both ladies greeted me at the door. Karen pushed herself against me and kissed me deeply. Karen's Mom stood back and smiled. Karen grabbed me by my hand and led me over to the couch. They both sat down. I was standing awkwardly and then Karen's Mom ordered me to strip. I really wanted to please her and immediately stripped. Karen's Mom then said that we first needed to come to an understanding. They only way we could be together was if I understood that the ladies are always in charge and that my role is to be used for their pleasure. They might grant me some pleasure but only after I demonstrated that I got it. She looked at me with her light blue eyes and I felt her gaze deep within me. I nodded that I understood. She order me to turn around and then grabbed the rope that was nearby and tied my wrist together behind my back. She then told me to turn around and tied a ball gag into my mouth. I stood by meekly. It just felt right to me. She then ordered me to lie across her lap. Karen's Mom had a leather paddle with holes in it next to her on the couch. She picked it up and showed it to me. She told me that it takes time to learn how to behave properly. She reminded me that it took me years in school to learn what I now know as a senior. She then told me that the way people learn is through reward and punishment. Karen's Mom then pressed me down with my head in Karen's lap. She then began to pound my ass with the paddle. Karen caressed my head and helped keep me in the proper position. The paddling really hurt and I began to cry and beg her to stop. She continued the paddling. Karen's Mom told me this paddling is to show me what the punishment would be if I disobeyed. She also said she likes paddling the Man's ass as it puts him in his place and turns her on. My ass felt on fire after the paddling. She removed my gag and pushed me off the side of the couch. She spread her legs and pointed to where I was to place my tongue. I eagerly complied. I felt so close to her and yearned to taste her. I ate her just as she taught me last time. I gently took her clit between my lips when I felt she was ready to cum. She grabbed my head with her hands and told me I was a good boy. Her praise inspired me. Karen had opened her legs on the other side of the couch. Karen's Mom pushed my head over and pointed to Karen's bald pussy which was on display. I could see and smell her arousal. I moved over and pleasured Karen as I was instructed. She arched her back and cried out when she came and praised me for my service. I was more aroused then I had ever been in my life. Karen's Mom said that this was just the appetizer. They stood up and helped me to my feet. Karens's Mom grabbed me by the cock and led me into her bedroom. I noticed there were ropes tied to the four ends of the bed. She led me to the foot of the bed and had me face the headboard. She untied my wrists and told me to lie down on the bed on my stomach. They each grabbed an arm and tied my wrist to the top corners of the bed. Karen placed two pillows under my stomach which lifted my ass off the bed. My legs were then tied to the bottom two corners of the bed. The ball gag was reinserted into my mouth. I felt the sting of the paddle on my already beaten ass. I pulled against the ropes but could not move. I then felt Karen's Mom use her fingers to spread my ass cheeks and felt a lubricant being applied to my tight asshole. She told me that my ass was for their pleasure. This included being spanked and fucked. She told me that being fucked puts the man into his right place and that it turned her on to see the man suffer for her. Karen's Mom then began inserting a small dildo into my ass. She would work it around. My ass felt surprisingly good. It took a little while to get used to it but it was not an unpleasant feeling. Then Karen's Mom moved to larger dildos. She lubed my ass again with her fingers and inserted several fingers into my hole. I really felt it and moaned into my gag. She then put more lub on my hole and started with a much larger dildo. I felt my ass being spread open as she slowly and gradually forced the bigger dildo into me. I pulled against the ropes and moaned deeply but Karen's Mom keep pushing it in. Karen sat by my head and rubbed my hair and told me how well I was doing and that I would get a reward. Karen's Mom then worked the dildo further into me and I felt the butt plug fill my ass as it fit deeply into me. They left me when they left the room. Then soon came back each with a glass of wine and a wicked grin. Karen's Mom then paddled my ass again which hurt even more with the butt plug in me and my ass so sore from the other paddling. She told me I was doing well and more fun was to come. They untied the ropes and positioned me on my back with my ass at the end of the bed. My wrist were tied behind. I submissively complied as they rearranged me. I did not even think of doing anything but obey. Karen took a long drink from her wine and removed her dress. She was naked and then straddled my face. She order me to put my tongue in her pussy as she rode me. She grabbed the side of my head for balance. I could not see anything else that was happening. My next feeling was the butt plug being removed and more lubricant being put in my asshole. I then felt the hard shaft of the strap-on as it entered me. I raised my head and shouted out. Karen rolled off me and then slapped my face. She told me to behave as her Mom loved fucking her men. She then remounted me and told me to lick her asshole and that was what I must do to show her my devotion. I eagerly did that. I was lost in space (I realize now subspace) as I licked Karen's ass and pussy and felt her Mother pound my ass. Karen came hard again and climbed off my face. They then switched positions as Karen pouned my ass with the strap-on and her Mom pleasured herself on my face. Karen's Mom came several times as she filled me with her juices and I eagerly licked her pussy and ass. Karen then pulled her strap-on out of me and gave me a big smile. She me that I did well and that it was time for my reward. She surprised me when she climbed over me and placed my nipples in my mouth for me to pleasure them. I worked over each nipple as I was instructed. She then moved lower and grabbed my swelled cock. She moved back her pussy and placed my cock in her. It was heavaen. She told me how much she liked fucking when she was on top. She told me I deserved it as I had done a great time pleasuring her and her Mother. My release was extraordinary. I have to say it was the best one ever. I tried to reproduce that feeling many times and although I really enjoy cuming, nothing ever matched up to that feeling. My Journey To Submission moved forward. There was much more that came aftrwards which I will tell you in future stories. I felt then, and still feel now, how fortunate I am. My Journey to Submission Pt. 03 This is the third part of my story. Reading the other two parts is important to set up this part of my story. ***** My journey into submission was proceeding. I submitted to Karen and her Mom several times a month during my senior year at the midwestern university in the late 1970s. We would get together at the apartment they shared. Our times together became more intense and I became even more comfortable submitting completely to Karen and her mother. We would always begin by being greeted at the front door by Karen and her Mom. Karen would give me a kiss and then I would be ordered to strip. I was always to be naked in their presence. They created a shelf in the front hall closet for me to place my clothes. I would then walk over to the couch where they would both be sitting. The couch faced away from the door and towards the large window which looked out over the city. I would place myself across their laps and Karen's mom would begin the spanking. Karen's mom did most of the spanking and preferred to use her strong hands. She only used the nearby paddle when her hand tired. The spanking always would bring me to tears and I would just lie there and take it. They always used their strap-ons to fuck my ass. Karen's mom took the lead. She gradually expanded my asshole by using lubricant and larger devices. I would wear a butt plug during the remainder of our time together. They would thoroughly fuck my ass. I was always gagged and could do nothing but take it. I grew to crave the feeling of having my ass filled by their cocks. All the back and forth motion of the fucking was hard to take but I did it for them. Karen's Mom seemed to get more into the fucking then Karen did but they both used my ass as they pleased. I became an expert in using my mouth to pleasure their pussies and bring them to orgasm. They taught me many positions. Karen's Mom preferred to ride my face and Karen seemed to like it most when I laid between her legs on her bed. Karen would cum with loud moans and Karen's Mom would have multiple intense orgasms. During our last time together they taught me to pleasure them from behind. They got on their hands and knees and I was taught to first lick their ass and then pussy until they were pleasured. I became as good eating their asses as I was eating their pussies. Karen's Mom would use her cane on my sore ass whenever I disobeyed or did not pleasure them properly. I hated the cane (and still do). It really got my attention to serve them the way they deserve. They would grant me my release about half of the time. It was always Karen and never her Mom. Karen would then allow me to fuck her with her being on top. A few times she gave me a fantastic blow job. She decided when and how I was to be pleasured. It was all great and I always looked forward to our times together. I was well along my journey. It was getting closer to the end of my senior year. Karen had missed two classes and I was concerned. I finally saw her at a class and she did not look right. Something definitely seemed to be wrong. We talked briefly and made arrangements to have another time together later in the week. I missed being with them and was eager to serve them once more. I arrived at the appointed time and knocked on the door. Karen's mom opened the door. I walked in and was surprised that Karen was not there. I asked if Karen would be there and her mom said no and that she had me all to herself that evening. I then told her how beautiful she was and how I so needed to submit to her desires. Karen's mom was in her mid forties. She was shorter than Karen and had a few more pounds but I grew to I love the curves of her body. She had a lovely face and stunning light blue eyes. I even liked the way she wore her hair. Most of all was that she radiated a strength and eroticism that overwhelmed me. This started me on being most attracted to older woman. They had strength and passion. They used their experience to teach me to behave the right way. I told Karen's mom how I felt and she smiled and then ordered me to strip. I then walked over to the couch and laid across her lap as I always did to start our time together. Karen's mom then began my spanking. She started slowly and built up a rhythm. My ass took the pounding. I remember that this time she talked a lot while spanking my ass. She told me that a sub most always be spanked the right way. To her being spanked the right way meant that the sub would be brought to tears and have the pain last several days. She also told me that I was doing well and was beginning to understand. Initially my submission was all about me and what I wanted to do. I was doing it mainly for my pleasure. She told me real submission was when the sub did it only for the pleasure of the lady. The sub wants and needs to pleasure the lady by submitting to her desires. The spanking had to be 'real". She spanked me for as long as she desired. I really did now understand. I wanted her to be pleased with me. I knew I could get up and leave at any time but I could not and would not do that. Her praise meant so much to me but I most wanted her to be satisfied. My ass and mouth were really there for her pleasure. This spanking was the most intense one during our many times together. There was something else going on here. When Karen's Mom was finished she had me kneel in front of her and she guided my head to lay across her lap as she caressed my face and told me that I did well. She told me that I was ready for another step in our relationship. She then told me that I was to become her piss slut. I raised up my head and gave her a worried look. I never thought of doing that. She told me not be concerned. Drinking the piss of a healthy woman was not harmful in any way. I had already swallowed all of her fluids and nothing unhealthy has happened. She told me that my only choice was to do it or leave. I looked deep into her light blue eyes and nodded. She knew I could not leave. If I left then, I knew I would never see her again and I need to be with her. She then told me to stand and led me by my cock and balls into her bedroom. She always led me along by grabbing my cock and balls. It hurt but seemed right and always aroused me. We went into her bedroom. It was the first time I was in her bedroom. We had always gone into Karen's bedroom. Karen's bedroom was smaller and done all in pink and light colors. Karen's Mom bedroom was bigger. It was strong but yet feminine just like her. She led me by my cock and balls directly into her large bathroom. She opened up the door to the large walk in shower and told me to lay on my back with my head near the wall. I had to pull up my long legs to fit in. The cold tiles felt good on my sore and red ass. She removed her dress and squatted over me. She grabbed my hair and lifted my head and told me what was going to happen. She told me the most important things were to not breathe and to close my eyes. Getting piss in my eyes was not good and was not where it belonged. I was told to open my mouth and hold my breath until ordered to do something else. She said her piss would fill my mouth and when it was full that I would then get the order to swallow. She would have stopped her stream and watch me swallow her piss. She then reminded me about the breathing and eyes and then placed her pussy right next to my open mouth. Having her piss fill my mouth was one of the most erotic experiences of my life. It was warm, warmer than I thought it would be. It was strong but not too much to take. It was sour but yet tasted like her. I eagerly swallowed her piss as I wanted her to be pleased. I heard her moans of pleasure as she filled my mouth several times with her warm piss. I must have swallowed four or five times. Karen's mom kept pissing on me aftert the last time I swallowed. My head and hair was covered with her piss. Karen's mom then lowered herself on to my face. I placed my tongue deep in her pussy and took her clit between my tongue and upper lip. I moved my tongue deep inside her to clean her completely and caress her. She moaned as she moved her pussy and clit over my mouth. She told me to suck her clit as she came and came. Waves of her orgasm rolled over her. Karen's mom usually came quietly but this time she lost control as she came violently and rubbed her pussy all over my tongue, mouth and lips. I can't describe how good it felt to know that I pleasured her this way. She eventually rolled off me and laid next to me as she recovered. She then told me that I did well and that I was now her piss slut. She then rose up and told me to stand up. She turned on the shower and handed me the soap and wash rag. I soaped her up and washed her all over. It was so erotic. I made sure she was properly cleaned. When I was finished she had me dry her off. She put on her robe and told me to shower and wash my hair and use mouthwash. I was to then join her naked in the kitchen. I went to Karen's mom in the kitchen. She asked me if I was hungry and then made me a sandwich. We talked a long time. It was very comfortable and intimate. We talked about many things. We talked about life and current events. Karens' mom gave me advice about my forthcoming job interviews. She also told me that Karen was now in an alcoholic rehab. She was glad Karen was finally dealing with her depression and drinking. We talked long into the night. Karens' mom walked me to the door. While I was still naked she came close to me and told me I was her toy boy. She then kissed me. It was our first kiss as only Karen had previously kissed me. I allowed her to lead with the kiss and enjoyed it immensely. TO BE CONTINUED 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. ***** 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 My Journey to Submission Pt. 05 This is part 5 of my journey to submission. It would be helpful to read the previous chapters to understand the people and how we got to this part of the story. ***** I had a hard time sleeping. Karen's mom told me to spend the night with her and seemed to sleep well. My mind was racing and my body was aching. I kept thinking about last evening. Karen's mom and Lady Elena used me for their pleasure. I provided oral service to them. They gave me a very hard spanking on the kitchen table and Lady Elena tortured my nipples, cock and balls. My nipples hurt the most after being abused by hands and clamps. My cock and balls pained me from being tied up and from the clothes pins and steel wheel. I replayed all our activities and became even more aroused. I admitted that I both wanted and needed to be used by Karen's mom for her pleasure. I kept thinking about how wonderful her pussy tasted and how I craved her attention and satisfaction. Karen's mom was in her forties and I was finishing my senior year at the midwestern university. There was something about her that attracted me. It was the way she looked, smelled and combed her hair. It was her light blue eyes. It was mostly how she had a presence of erotic authority and how I wanted and needed to pleasure her as she desired. I was also thinking about the instructions I was given before Karen's mom feel asleep. I wanted to do exactly as I was told because I needed to pleasure her and I wanted to avoid the painful punishment from the cane if I failed in anyway. I must have dozed on and off but I was awake to watch the minutes turn slowly to 7:30am when I was to begin my instructions. I gently went under the covers towards the bottom of the bed. Karen's mom was sleeping on her left side. I gently began kissing the outside of her thigh and moved towards the inside of her thigh. I gently nuzzled between her legs and she slowly responded by opening her legs and moving to lay on her back. I licked her pussy as she taught me. I gently used my tongue to lick her from the bottom to the top of her slit. She tasted wonderful. I gradually increased the depth of my licking and how fast I went and how I paused at her clit. I felt her respond. Her juices began to flow and I heard and felt her moans. She began encouraging me by telling me how well I was doing. I responded by spending more time on her clit as I was instructed. I felt her orgasm building and was pleased when she shuddered and came. I kept gently sucking her clit as she continued to have orgasms. She then grabbed my head and moved my face to her thigh. We laid there in a warm intimacy. She told how this was a wonderful way to start her day. She was going to have me stay over more often so that I can be there to satisfy her morning needs. She then told me to switch positions with her and lay on my back at the top of the bed. She then reached over to her nightstand and said she had something else for her pleasure this morning. She then pulled out and showed me a large white cock which had an elastic strap attached to its base. There was an indentation at the base of the cock. I was not sure what this was to be used for but soon found out. She placed the elastic around my head and the base of the cock on my chin. Karen's mom then put some lotion on the entire cock. She then rose up and straddled my face and the cock. She told me that I had to follow her instructions. I was not to touch her in any way. She then grabbed the base of the cock with one hand and placed her other hand on the top of the bed frame. Karen's mom then gently moaned as she gradually inserted the cock into her wet pussy. Her moans told me how much she was enjoying using me in this way. When the cock was fully inserted then I realized the other role I was to play. My tongue reached out and began caressing her clit. Karen's mom began moving up and down the cock and telling me to suck her clit harder. She told me when I was sucking her clit just right or too hard. I wanted to use my arms to grab her ass and make us even closer. I knew I was told not to do that but I could not resist. My arms reached up and held her ass closer to me. She immediately pulled back and slapped my face hard. She told me that only she controlled how I was used. I would be punished for disobeying. I was angry at myself but understood. She soon regained her motion on the cock. My tongue and lips were used on her clit to bring her to a long series of orgasms. Karen's mom then climbed off my face and laid next to me for a few minutes as she recovered. She then looked at the clock and stood up. She told me that it was now time for her piss slut. As her piss slut I was to be used to take her piss. No more cold toilet seats while I was there to serve her. She ordered me to follow her into the large walk in shower and to bring along the used cock to be cleaned. She told me this time to sit on the tiled floor of the shower with my back up against the front part of the shower. She reminded me of my training as her piss slut that I was to not breathe until ordered to swallow her piss and that I was to keep my eyes closed to not get any of her piss in my eyes. She stood over me and told me she did not feel like squatting this time. She then grabbed my jaw and tilted back my head as my mouth opened. She then stood over me with a look of satisfaction and arousal. She then pissed directly into my mouth. After my mouth was full of her warm piss then I was ordered to swallow. It tasted her. She kept pissing all over my face and head as I swallowed. She then ordered me to open my mouth again and take more of her piss. I was ordered soon to swallow again and she continued to piss all over my body. I felt great having had satisfied her as her piss slut. She stood back when she was finished with a look of pleasure on her face. She then told me to stand up and place my hands on the wall of the shower and to stick out my ass. She told me to close my eyes. I heard her leave for a moment and then return. The next thing I heard was the sound of her cane. I then really felt the sting as her cane crashed into my already sore ass. I hated that cane and still hate the cane today. She gave me six hard hits with the cane. She paused and hit me six more times. I was crying and begging her to stop. With each hit she told me that I disappointed her by before touching her on the bed. I felt bad for disappointing her and felt especially bad as it really hurt. I took it as I know I needed to be punished and get better at pleasuring her. Karen's mom then turned on the water. She told me to wash her with soap and a hand cloth. When she was finished she told me wash myself and the dildo. I was to then take care of my bathroom needs and use mouthwash. She told me to return to her bed and lie on my back at exactly 8:20am. I did as I was instructed. Karen's mom soon came into the bedroom wearing a simple sundress. She had me stretch my arms and legs to the four corners of the bed. I was quickly restrained me to the bed on my back with my arms and legs tied to the four corners. She returned the clean dildo to its place in her nightstand drawer. I noticed she looked at the clock as she rose to the top of the bed and straddled my face. She turned around to face my feet. She pulled up her dress and told me to adore her ass and to not touch her pussy. I eagerly placed my tongue deep into her asshole. It somehow felt good and right. I moved my tongue around as she moaned. Karen's mom told me she had some very interesting activities planned for me this morning. After several minutes of enjoying my tongue in her ass she then she rose off me and off the bed. She then grabbed a red ball gag from her drawer and tied it tightly in my mouth. She smiled as she placed a gentle kiss on my cheek and told me not to go anywhere. She noticed my huge erection. She slapped it and told me that this was all for her pleasure and not mine. She mentioned something about reminding me soon about understanding my role. Karen's mom left the bedroom door open after she left. I heard her in the kitchen as she seemed to be making coffee and arranging a few things. I thought back on how much I enjoyed the morning so far and was wondering what else would happen. I then heard the door bell. I was stunned. I wondered what was going to happen. I could not see the front door through my open bedroom door. I soon heard voices. I listed closely and then determined there were two new voices. I heard the name of Mary. I heard the voices moving away from the front door as they moved into the kitchen. I listened even more closely and could follow some of their conversation. Apparently they got together every week at this time in one of their homes. I heard them talk about their recent activities and what was going on in the neighborhood. I wondered whether they would soon all know that I was naked and tied to the bed in the other room. I eventually heard a voice say that she did not believe what Karen's mom said previously about her having a toy boy. She asked Mary what she thought. Mary said that Karen's mom was always the wild one and that it might be true. The first voice said that she also has her wild side but that seeing is believing. Karen's mom then told her that she already used her toy boy today to provide oral service and that her toy boy was also well trained to provide other very enjoyable services to her. The other voice doubted her once again. I heard Karen's mom rise out of her chair and laugh. She told them that her toy boy was tied naked to her bed and that she recently used him for her oral pleasure and to take her morning piss. They all started to talk again. I could not pick out what was said but I soon heard them all rise and move towards the bedroom. The first person who came into the room marched right up to the bed and placed her arms on her hips and shook her head. She was a tiny older woman. She must have been over 70. I then heard her name was Birdie and she looked like it. She was small with thin arms and legs. She had a head of big grey hair and a sharp pointed nose. The other woman, Mary, was much larger with wide thighs and long jet black hair straight down her back. I guessed she was in her fifties. She placed her hand to her mouth in disbelief. The woman were then told in great detail how I had been used today and the night before. I sensed that they were getting aroused. Birdie apparently knew Lady Elena and her reputation. Karen's mom then pointed towards my growing erection and said they can all help her teach me a lesson. Karen's mom walked to her dresser and grabbed a large wooden ruler. I remember that the ruler had a thin metal edge. Karen's mom then came over to the bed and swung the ruler to beat my erect cock. The woman all laughed at my distress. I could feel my cock turning black and blue from the pounding. It really hurt but my cock was still hard. Karen's mom asked if anyone else wanted have a few whacks. Birdie immediately came forward to take the ruler. She then grabbed the base of my cock and began giving it short hard strokes from the ruler. She beat my cock like a drum as I moaned deeply into my gag. Karen's mom then asked Mary if she wanted a turn. She said she wasn't sure but they convinced her to give it a try. Mary initially was not sure of herself but soon got into it and took it out on my cock. My erection did disappear and Karen's mom told me that this is a reminder that I am here for her pleasure and not mine. Birdie then surprised everyone by asking Karen's mom if she could fuck my ass. Karen's mom asked if she had done it before. Birdie said that she and her late husband Henry had played before he passed a few years ago. She said she now realized how much she missed it. Karen's mom smiled at her and directed the three of them to follow her back into the living room. I waited not knowing my fate but I felt aroused and wanted to show them that I was devoted to Karen's mom and would do as I was instructed. Birdie soon came back into the bedroom and closed the door. She smiled at me as she went to the dresser drawer and took out Karen's mom large ten inch black cock and harness. Birdie was very verbal and I found out that she loved to talk dirty. She told me that I was her bitch during our time together and I that I would get the fucking I deserved. She told me to take it or she would tell Karen's mom that I disappointed her. She told me how she knew I hated the cane and hated to disappoint Karen's mom. She undressed and then untied me from the bed but kept the gag in my mouth. She had me get on my knees and elbows with my ass at the edge of the bed. She then put on the harness and lubed the cock and my hole. She liked pushing her fingers deep into my ass and move them around. She seemed to get aroused by my torment. Birdie then lined up behind me and immediately pushed her huge cock deep into my asshole. She let out a moan and she fucked me with deep long strokes. She left the cock deep in me and told me to fuck myself with it. She held the cock in place as I rocked back and forth as I adjusted to its size. Karen's mom trained me well. She seemed to cum herself and she then pounded me even harder. Birdie eventually removed her cock and harness. She sat at the edge of the bed. She spread her thin legs and told me to kneel in front of her. She leaned back and told me that this better be the best pussy eating of her life or she would tell Karen's mom and I would feel her anger. She then told me she was going to ask Karen's mom if she could use me often for her pleasure. I then began as I was instructed. Birdie responded immediately with deep moans and grinded her pussy in my mouth. She grabbed my hair and told me she wanted me for a weekend. She told me how my mouth and ass would get a workout. She thought Karen's mom would allow her to use me. When she came I had to work hard to swallow it all. I then kept licking and Birdie kept moaning. She said again how she had to have me as her own. I know Karen's mom would decide and that I would do whatever she wanted me to do. TO BE CONTINUED My Journey to Submission Pt. 06 This is the sixth part of my journey to submission. I suggest reading the previous parts to understand the people and how we got to this part of my story. ***** Birdie tied me on my back by my arms and legs to Karen's moms' bed. She left me in the position she found me. She had just used my ass and mouth for her pleasure. Birdie was a thin woman with big grey hair who had to be in her seventies. She fucked my ass with the ten inch black strapon and made me eat her pussy until she came. My thoughts were spinning and my ass was hurting after she left me. I was in my senior year of college and was being trained to submit to Karen and her mom. Karen's mom was in her mid forties and totally captured me with her looks and attitude. Karen was the former older girlfriend of someone I knew at the midwestern university. She introduced me to her mom and that began my journey to submission. Birdie and Mary had joined Karen's mom at her apartment this morning. Karen's mom and Mary soon opened the bedroom door and walked into the room. Karen's mom looked pleased and Mary looked excited. Mary was probably in her fifties. She was a heavy set woman with large thighs and long dark hair. Karen's mom told me that Birdie gave me a good grade and that it pleased her that I demonstrated my submission to her and her friends. Karen's mom then told me that Mary needed some special attention. She explained how Mary had not been with anyone for a long time and that she had never used a boy toy for her pleasure. Karen's mom said that they discussed what Mary wants to do and that I must comply to Mary's orders as if they came from her. Karen's mom then untied me from the bed and had me kneel down in front of Mary who had sat on the edge of the bed. Karen's mom rubbed the top of my head as she left and told me to be a good boy. She closed the bedroom door as she left the room. Mary looked at me and I saw the sparkle in her eyes. She told me that she has been thinking about this for a long time. She told me to then climb up on the bed and lay over her lap. Mary stroked my sore and red ass. She told me that she heard I was a bad boy this morning. She said that sometimes Mommy had to punish her bad boy. That it was Mommy's role to teach her bad boy how to properly behave. She said that she did not want to punish me but that I must get what I deserve. She then brought her hand down hard on my ass. She pounded my right cheek three times and then did the same to my left cheek. The spanking really hurt as it was on top of the previous spankings and caning. She paused and rubbed my ass and told me again that Mommy was sorry that I had to be punished. She once again spanked my left ass cheek three times and my right cheek three more times. I began to cry and beg her to stop. I told her I learned my lesson and would be a good boy. This seemed to arouse Mary more and she continued to spank me hard until her hand got tired. After she was finished I laid across her lap and felt her caresses on my sore and red ass. She then told me to stand. Mary rose and then looked me over and smiled. She said that Mommy really enjoyed having her breasts suckled. She also said that the bad boy should want to make Mommy happy after he misbehaved and had to be punished. She removed her blouse and bra. Her tits were huge with large erect nipples. She laid back on the bed and motioned me to lie next to her with my mouth near her left breast. She stroked my hair and told me that I must show Mommy that I really am a good boy. Mary then directed me to suck her large nipple. Karen's mom was not interested in having me suck her breasts but Karen was very much into it. Karen instructed me during our previous time together so I knew what was to be done. I gently took her nipple in my mouth and rolled my tongue around it. I began to gently suckle on the nipple. Mary immediately responded by feeding me more of her breast and moving her hips. She told me to be a good boy and suckle Mommy. She said that I should use her breasts as udders to get my milk. She encouraged me to suck her harder and to then take more of her breast into my mouth. She kept caressing my head and told me I was being a good boy. I could tell Mary was getting very aroused. She had me eventually switch sides and soon I was sucking her right nipple and breast. I understood exactly how hard Mary wanted to be sucked and took more and more of her large breast into my mouth. My mouth was aching but it felt right to please her. I wanted Mary to tell Karen's mom that I did well. Mary kept talking to me about how a good boy does what Mommy wants. She said she often pumped her breasts while at home and wants to produce milk for her boy to be nourished. No milk came out but I continued to suckle her nipple and then take in as much breast as I could fit into my mouth. After a long time Mary gently told me to stop and that I did well. She told me that Mommy now wanted something else from her good little boy. Mary then unfastened her skirt and pulled down her large white underwear. Her pussy was hairy but I could see the moisture on her slit through her dark pussy hair. She told me that Karen's mom said that I should not be allowed to cum but that she wants to feel my little dickie inside of her. Mary grabbed my face and looked deep into my eyes. She told me not to cum or that there will be a severe punishment. She then told me to move down into the position to put my little dickie inside of her. My dickie was definitely not little but was fully erect after all of the breast sucking. I knew that fucking her and not cumming would be really hard but that I had to obey her. I moved myself to be between her legs as Mary spread them wider. I grabbed my cock and put it gently in her wet slit. I very slowly pushed it into her pussy as her pussy was so tight. It was still a tight fit even though Mary's juices were flowing. Mary moaned deeply and told me how good my little dickie felt inside of her. She told me I was a good boy and was making Mommy very happy. I began to slowly fuck Mary with long strokes. She moved her hips back and forth and let out moans of pleasure. I was trying to think of everything else instead of what I was doing. I knew that I was not supposed to cum. Mary was moaning even more and eventually screamed that she was cuming. I continued to fuck her through her orgasm. I could not hold it back anymore. I knew it was wrong but my body could not stop. Feeling Mary cum pushed me over the top and I filled Mary with my semen. Mary knew what happened and began to hit me on the side of my head. She called me a bad boy and that I will be severely punished. She pushed me back and slapped my face. She then closed her legs and grabbed a blanket to cover herself. She then called out to Karen's mom that there was a problem. Karen's mom and Birdie came rushing in. Mary said that I disobeyed and came inside of her. Karen's gave me a look that I still remember. She was furious and I felt so ashamed that I disappointed her. Karen's mom looked over the situation. She said the first thing was that I must now eat all of my cum out of Mary. She then turned around and led Birdie out of the room. Birdie said that she was also angry at me and that I was really going to get the punishment I deserve. Karen's mom then told Mary that she should let her know when I was finished eating my own cum. Just before she closed the door she told Mary that she was also angry with her for putting all of us in this situation. Karen's mom said that she will deal with her later. Mary seemed upset and worried. Yet I sensed something else from her. Maybe that was a smirk on her face. I did not have time to think it over as Mary spread her legs and told me to clean out all my cum. I placed my tongue deep inside her pussy and soon tasted my own cum. TO BE CONTINUED My Journey to Submission Pt. 07 This is the seventh part of my journey to submission. I suggest you read the previous parts to understand the people and how we got to this part of my journey. ***** It was really hard to eat my own cum out of Mary's pussy. I had just cum inside of her so my erotic energy was low but I was only 20 years old and was still very aroused by the morning's activities. I was upset about disappointing Karen's mom but I did what she told me to do. My tongue was deep into Mary's pussy and I licked and cleaned out our cum. Mary responded by moving her hips and grabbing the back of my head. I was a 20 year old college student in my senior year at a midwestern university in the late 1970s. I had met Karen and her mom and they led me on my journey to submission. I became especially close to Karen's mom and still retain that urge of being with older woman. Karen's mom was so erotic and beautiful and she taught me how to behave properly as a submissive. I was upset because I disobeyed her by cumming inside of Mary when I knew that was not allowed. Karen's mom opened the bedroom door and strode aggressively into the room. She said that I must be finished cleaning my own cum out of Mary. Mary nodded and tried to cover herself up as I withdrew my head from between her legs. Karen's mom was furious. She took immediate command of Mary and the situation. Karen's mom told Mary that she had violated her trust. They had agreed upon what Mary could make me do and that it did not include me fucking her and that she was clear that I was not to cum. Karen's mom told Mary that only she decides when I could cum and that Mary put me in a very difficult situation. I was to be punished for disobeying the order not to cum but that Mary must also be punished from violating the trust Karen's mom placed with her. Karen's mom also said that she understood that Mary really wanted to be used by her and that she would not tolerate topping from the bottom. Mary was going to be punished in a very severe way to made it clear that she was not getting what she wanted. Birdie was watching from just inside the bedroom door and glared at Mary. Birdie told Mary she respected what Karen's mom had entrusted her with and that she did not violate that trust. Karen's mom then told us to remain naked and directed us to the living room. Mary seemed embarrassed by her nudity as she was a large woman in her fifties with huge breasts. We put our heads down as we walked into the living room. We were then directed into the spare bedroom which was being used as an office and exercise room. There was a bench in the room that was used to lift weights. It was all black with a thick pad and iron bars which connected the base of the bench to the ledge where the weights sat over the top of it. A strong wide wood board was placed on the ledge where the weight bar would have been. Mary meekly followed us all into the room and was told to sit on the bench with her back to the iron bars and wooden ledge. Karen's mom immediately tied ropes to her arms and legs. She then tied Mary's arms to the wood board on the ledge behind her. These ropes were tied in a way that pulled back Mary's shoulders which caused her huge breasts to stand out even further. Her legs were tied to the bottom legs of the bench in a way that separated her wide thighs and displayed her pussy with its thick black hair. Mary was completely vulnerable and seemed to be in a trance. Karen's mom tied a black ball gag in Mary's mouth and told her again why she was being punished. She reinforced that she was in charge and that the punishment would be severe. Karen's mom then tied a smaller rope around the base of each of Mary's breasts. She pulled and tied the ropes to be so tight that the pressure on Mary's breasts made them a deep red color and it looked like they really hurt. Mary moaned deeply into her gag. Karen's mom then grabbed a long handled flexible paddle. It was black and had a small rubber pad at the end. It looked like it would really hurt. I had not seen that paddle before. Birdie and I watched intently from the corner of the room. Karen's mom stepped towards Mary and grabbed her hair. She told her again that she was being punished for violating her trust. She began pounding Mary's defenseless breasts while pulling back her hair. The huge breasts took a beating. The sound reverberated throughout the room. Mary moaned and cried as her breasts were beaten. Black and blue marks soon appeared all over her breasts. Karen's mom gave special attention to Mary's large nipples. She stood in front of them and swung the paddle to just hit the tip of each nipple. This seemed to affect Mary the most. Mary moaned and cried and shook her head back and forth. Karen's mom eventually stepped back and was breathing heavily. She said that she wanted Mary to remember this for a long time. She put down the long paddle and reached into a black bag. She produced a short handled whip. I remember her eyes gleamed as she displayed the whip. Mary cried even more and shook her head and pleaded through her gag. Karen's mom just smiled wickedly as she strode towards the helpless black and blue breasts. She carefully measured her distance and gave a perfectly placed whip mark on the four sides of each breast. Mary responded with deeper moans and cries. Birdie and I watched and I could feel Birdie's growing excitement next to me. Karen's mom stood back and then looked Mary deep in her eyes. I saw that there was now a deep connection and that Mary really needed to submit to Karen's mom. I realized then that Mary had used me to be with Karen's mom in this way and it really bothered me. Birdie told Mary that she has gotten into much more than she could handle. Mary was untied and collapsed into a chair in the corner of the room. She held her head between her hands and said how sorry she was and that she understood that the punishment was deserved. Karen's mom went to her and whispered something in her ear. I heard part of it and it was clear that Mary would soon be learning how to properly pleasure her. Karen's mom then turned her attention to me. She told me to sit on the bench facing the opposite way that Mary was positioned. I faced the wooden board that was on top of the iron side bars. Karen's mom stood in front of me and she looked so beautiful. She was soft yet strong. She had an intensity to her light blue eyes that completely captured me. I so wanted to please her and be what she wanted me to be. She then told me how special the bond is between the Mistress and her sub. How trust was an essential part of this incredibly special and unique relationship. Karen's mom told me she valued my devotion to her and that she accepted her responsibility to nurture our deep connection. She would guide me and protect me. She realized she had made a mistake by entrusting me temporarily to Mary and that would never happen again. She understood how I had to obey Mary as I was told to so. However I must still be punished for cumming when I was told that it was not allowed. My punishment would remind me once again that my role is to obey and serve my Mistress. Karen's mom went to the closet and soon came out with the largest butt plug I've even seen. It was much bigger then what I had ever taken. Karen's mom walked over to me and ruffled my hair and caressed my face. She intensely looked at me as she told me to sit on this butt plug and take it all in for her. She motioned me to stand up and then attached the huge butt plug to the bench. It was then lathered with a large amount of some creamy substance. Karen's mom stood in front of the bench and never looked more beautiful to me or more in command. Our eyes met and there was this deep connection that was almost overwhelming. I recall that there was nothing else in the room or our lives at this moment. I slowly moved down to take the small tip of the plug into my ass. I was not and did not need to be restrained. I soon felt my ass being stretched as I moved a bit further down on the plug. Karen's mom eyes encouraged me and showed me that she understood how hard this was for me. That gave me the extra incentive to keep pushing down as the butt plug tore into my ass. The cream on the plug really helped me take it all deep inside of me. I kept pushing down while never breaking eye contact with Karen's mom. The feelings when I finally felt when the plug completely fill my ass are hard to describe. There was so much pain, satisfaction, and relief. My ass felt painfully stretched but it did feel so good to have it so full. Karen's mom smiled and blew me a kiss. She then proceeded to publically claim me as hers. She kept eye contact until she raised her dress over her head to be completely naked in front of Birdie and Mary. There was a chair on one side of the bench and a table across from it that she moved into the right position. Karen's mom then stood on them and rested her back against the wooden board on the ledge. Her beautiful pussy was right in front of my face. We both knew that Birdie and Mary were watching intently. Karen's mom then told me to put my tongue deep inside of her and suck her clit. I eagerly did as I was told. She tasted so good. My upper lip massaged her clit while my tongue went as deep into her pussy as it could. Karen's mom held the back of my head and ground her pussy into my mouth and face. She came with an explosion and kept cumming as she moaned deeply and told me that I was such a good toy boy. I could not have been happier. My Journey to Submission Pt. 08 This is the eight part of my journey to submission. I suggest you read the previous parts to understand the people and how we got to this part of my journey). ***** The past few weeks with Karen's mom were wonderful. We fell into a comfortable and cozy pattern with my complete submission to her. I went over to her home several times each week. My submission to Karen's mom became more sexual. We were both so very comfortable in our roles. I would always immediately strip to be naked in her presence and she would take me over her lap for a spanking to put me in my right place. I then willingly submitted to all her sexual desires. She seemed to be especially aroused and horny during those two weeks. I loved eating her pussy and I always brought her to multiple orgasms. A new favorite position of hers was when I sat on her large comfortable sofa with my head against the back cushion. She would stand up on the couch facing me and would grind her pussy against my mouth. My tongue would enter her pussy and my lips would caress her clit. She would grab my head and look out through the large picture window as she rode me hard. She fucked me often with her strapons and also used various dildos including chin and mouth dildos. We both enjoyed our sexual intimacy and then had good conversations about everything. Well I should say that she enjoyed it much more than me because she had me in chastity the entire time. Karen's mom placed my cock in the chastity cage at the end of our time together with Birdie and Mary. The cage drove me crazy. I was a senior in college and was used to masturbating often to release my sexual energy. My erect cock pressed painfully against the cage. I was able to piss through the opening but I had to be so careful that other people would not see the cage. I had to shower at unusual times and made sure I peed in the toilet stalls instead of the urinals. I repeatedly asked her to remove the cage but she just smiled and said it was part of my training and punishment. My lust drove me crazy. This was especially true when Karen's mom told me stories about being with Mary in between our times together. She said she had never been with another woman in this way but she really enjoyed it. She found Mary really needed and savored the release of being taken by her. She said that Mary really thrived on severe breast torture and very eagerly learned to pleasure her pussy. Mary served Karen's mom in this and other ways for many years. I drove over to Karen's mom one Friday night about a month before graduation. I hoped that she would unlock my cock cage and grant me a release. I drove the 1965 Ford Comet that my grandfather had given me. Do you remember the manual transmission with three on the tree? I parked in my usual space and knocked on the door. I was shocked when the door opened and both Karen's mom and Karen were there. Karen looked absolutely stunning. My mouth dropped open and I could hardly talk. It is hard to describe how gorgeous she looked. She had lost weight and toned up while she was in the alcoholic rehabilitation. Karen was not heavy before but now looked leaner and stronger. She wore a simple short blue dress that displayed her strong arms and legs. Her sharp cheek bones were nicely framed by a new hair style. Her skin complexion was clearer and her light blue eyes more alluring. She was absolutely stunning. Think of Cameron Diaz in There's Something About Mary. She smiled at me and told me that she was so fucking horny. She told her mom that she wanted me immediately naked, spanked and in her bedroom. To have this gorgeous woman want me made my erect cock get even harder as it tried to burst through its confinement. I stripped as fast as I could. I managed to somehow tell her again how beautiful she was. Karen and her mom laid me across their laps on the couch and playfully spanked my ass. Karen told me again how horny she was and how she was going to make me satisfy all her desires. After a shorter than usual spanking I was told to stand up. Karen rose and kissed me deeply. She then grabbed me by my cock cage and led me into her bedroom. I don't think I ever had greater anticipation over what was going to happen to me. I asked her if my cock cage would be removed. She smiled and said that she wanted my cock but that I might not like what she had planned for it. Karen's mom called out to Karen to not do anything that she would not do. Karen laughed and said that left her many delightful ways to use her toy boy. Karen rushed me into her room and closed the door. She told me to kneel on the floor facing the side of her bed. She stood in front me and pulled her short dress over her head. She was then totally naked. Her body was gorgeous. Her huge breasts stood out from her tight body. Her abs and thighs were strong and the scent of her arousal filled the room. I told her again how beautiful she was and how I was eager to serve her in any way. She told me she thought about taking me all of the time and how much she now wanted to use my mouth, ass, and cock for her pleasure. She then sat on the bed and laid on her back. She spread her legs wide and moved closer to the edge of the bed. When she put her hands behind her head her breasts stood out even further. She told me to use my mouth to devour her shaved pussy. I was not to allow any other parts of our bodies to touch. She only wanted to feel my tongue and lips on her pussy. I eagerly began to pleasure her as I was trained by her and her mom. I immediately buried my tongue deep into her ready pussy. She squealed with delight. She soon told me to suck her clit. I heard her shouts of joy as she came all over my mouth. I had to suck rapidly to take in all of her juices. She then directed me to lick her slit from bottom to top and to slowly use more pressure. She then directed me again to her clit and I soon swallowed even more of her juices. All the time she was moaning and telling me how she missed using me in this way. After several orgasms she finally rose up. Karen caressed my head and held me close to her heaving breasts. She told me that this was just the appetizer. She told me to lie on the bed on my back with my head on her pillow. She walked over to her dresser and I admired the view as she bent over to get some things out of her dresser drawer. Her tight round ass was the best I've ever seen. She asked me if I enjoyed the view and I said once again that she was so stunningly beautiful. I could not see exactly what she was doing by her dresser but I heard her put on some plastic gloves. I then saw her grab a tube of something with a green and red label. She kept it hidden in her hand as she strode towards the bed. She told me it was now time to unleash my beast. I was so eager to have that damn cock cage removed and told her so. She smiled and said I might feel differently in a few minutes. Karen reached into the nightstand and took out a small silver key. She unlocked cage with a flourish and smiled as she grabbed my fully erect cock. It was definitely the biggest erection I ever had. Karen stroked my cock and told it she had some special plans for her enjoyment. I almost came when she tenderly kissed the end of my cock. Karen told me to close my eyes and place my hands behind my head. I was to keep my hands behind my head no matter what happened. She reminded me that I was hers to use and that any misbehavior would be severely punished. Her mom told her about all the adventures with Birdie and Mary. I was reminded that the bench and huge dildo were still in the other room. They discussed how my next punishment would include inserting the huge dildo in my ass and tying me to the bench. My defenseless cock would then be beaten black and blue with the ruler. I shook my head and said I would be a good boy. She laughed and reminded me to keep my eyes closed and my hands behind my head or she would tie me down and punish me later. I soon felt a creamy substance being rubbed into my shaved cock and balls. Initially it felt good to have Karen stroke my erect and eager cock. That feeling did not last long. My cock and balls began to burn. It took all my training and will power not to move my hands to stop the torture. She had rubbed bengay all over my cock. She laughed when she saw my torment. It burned. I cried out as she continued to rub in the bengay and my cock absorbed more of the ointment. Karen eventually stopped and ordered me to open my eyes. She positioned herself to be on top of my chest and fed her erect nipple into my mouth. Karen loved having her breasts sucked and moaned deeply as I eagerly sucked both of nipples. It did help me take my mind off of my burning cock and balls. Karen then leaned back and reached out to her nightstand to grab some lube and a condom. I soon found it was for her pleasure and not mine. She rolled the condom on to my burning cock which make it hurt even more as there was no air circulation to help disburse the bengay. She moved back on me and took my erect cock in her hand and placed it at the opening to her wet and wanting pussy. She told me to be a good boy and not to cum until she allowed me. Cuming was not going to happen now as my cock burned and it was always much harder for me to cum while wearing a condom. Karen then rocked back and forth on me as my cock entered her. I had a complex set of feelings. My cock burned but it wonderful to have it out of its cage and inside Karen. Her mouth found mine and we kissed deeply. Karen's mom never kissed me after I ate her pussy but Karen seemed to really enjoy it. She rode my cock and used her strong legs and upper body to make me fuck her deeply. She moaned the entire time and shouted when she came again. She then kissed me deeply and told me how much she missed me and our time together. Karen rose and playfully touched my aching cock. She then told me to again close my eyes and not go anywhere. She went into her bathroom and soon came back with a damp cold wash rag. Karen removed the condom and washed my burning cock. It felt so good to have some of the bengay removed and to feel the cool air on it. She then playfully kissed to tip of my cock. Karen grabbed another condom from her nightstand and rolled it over my cock. I felt some burning but it wasn't too bad. She went to the door and called out to her mom that it was time for their grand finale. Grand finale I thought, this should be interesting. Karen's mom then appeared. She was totally naked except for her huge black strapon cock. I remember how initially I was scared by that size cock but by now I was well trained to take it deep into my ass. It feel so good to have my ass feel so full. They walked over to me and Karen described what we had just done and how great it all felt to her. Karen's mom said I was a good toy boy and that I deserved a reward for all of my good behavior. She was stroking her cock as she smiled at me. Karen's mom took charge. She positioned me at the bottom of the bed on my knees and elbows with my ass hanging over the edge. She went behind me and lubed my asshole and her cock. She positioned me so that she could stand and comfortably fuck my ass. Karen laid naked on her back in front of me and placed her hands behind her head on her pillow. Her pussy was close to my face. She then pointed at her bald pussy and told me to get busy. I bent over and began licking her lovely pussy. She tasted so good. I soon felt Karen's mom pushing her cock against my asshole. The strapon went in easy for the first few inches and when she pushed harder it went deep into my ass. It was quite a feeling having Karen's mom fuck my ass while I was eating Karen's pussy. Karen pulled me even closer to her and soon they were both moaning their delight. Karen's mom told me she had placed a clit stimulator on the inside of the strapon and that she was especially enjoying this fucking of my ass. Karen eventually grabbed my head and told me to stop. She pushed herself away from me and moved further up on the bed. Karen's mom kept her cock in my ass as she told me to crawl forward. She now climbed up on the bed behind and told me to keep crawling forward. I was eventually face to face with Karen. She had brought her knees up and kissed me deeply as she reached down to grab my cock. Karen had just reached for some lub on her nightstand to moisten the condom. She then inserted my erect cock deep into her pussy. Karen's mom helped by pushing from behind. I now had Karen's mom's cock deep in my ass while my cock was deep into Karen's pussy. Karen told me that I could cum whenever I wanted. This was the best I have ever felt in my entire life. Karen's mom grabbed my hips and pulled her cock partially out of my ass. This pulled my cock partially out of Karen's pussy. When Karen's mom fucked my ass it caused my cock to fuck Karen. It was fantastic. We kept up this pattern of Karen's mom fucking me which caused me to fuck Karen's pussy. We were all moaning our pleasure. Karen and I kissed deeply. We fucked like this for a long time but it seemed too short. I felt their orgasms building as I felt mine growing. I would have cum sooner but the remains of the bengay and the condom delayed my release. I first felt Karen's mom cum and then Karen. Then I exploded. The weeks of chastity and the cock torment disappeared in a moment as I came as much as I possibly could. Karen's mom pulled out and rested for a moment at the end of bed. I laid next to Karen. Her mom came to us and stroked my head as she said it time for her to leave. I understood that she meant this both physically and emotionally. She closed the door as she left. Karen and I cuddled together and caressed each other while kissed again. We then had an incredible talk. We both completely opened up about our lives. We shared so much physically that it was natural now for us to share so much of ourselves emotionally. It was so incredibly intimate. I realized it was the intimacy that kept me coming back for more. Karen talked about herself and her struggles with alcohol. She talked about what caused it and what she learned about herself in recovery. I talked about my submission and why it felt so right to me and why it was so important to me. It just seemed natural that as we talked about our individual future plans that they began to come together as one. Karen wanted to leave her hometown. Her plan was to work as a paralegal and then go to law school. I was making my decision on where to take my first job and we both were thinking about the same east coast city. We talked long into the night and fell asleep together. That was when we both first fell in love with each other. I awoke the next morning and gently woke her by licking her pussy. She grabbed my head and shouted as she came. She then had us reverse positions and told me that she will always be on top when we fucked unless her Mom's cock was buried in my ass. That was alright by me. During our pillow talk afterwards we somehow decided that my pet name for her would be Tasty. I had told her before that her pussy tasted so good and she liked being reminded of that. I only use that name in private or when we are with Karen's mom. There were many other wonderful times together with Tasty, Karen's mom, Lady Elena, Birdie, and Mary. Karen's mom told me later more about her introduction to being a Domme through Lady Elena and her husband Bob. I might someday tell you those stories. Later that morning over breakfast we talked with her mom about our future. She was very supportive of us as a couple. Karen's mom eventually met a nice man named Gordon who became her lifelong submissive partner. I never again submitted to Karen's mom unless Karen was present. We all had some fantastic times together. As I left that next day I asked Karen's mom what I should now call her. Calling her Karen's mom did not seem right anymore. She laughed when Karen told her that I now call her Tasty. She said calling her Pussy Galore might have been right fifteen or so years ago in the early sixties but that it isn't right anymore. She suggested I call her Kitty and Kitty was what I called her. She was the best mother a toy boy could ever have. My Journey to Submission Pt. 09a This is another part of my continuing journey to submission. This is a standalone story but I suggest you read the other parts to understand the people and how we got to this point of the journey. There is piss play in this story. ***** There I was. I was naked and tied down on my back to a narrow padded bench in Berlin. My knees were spread on both sides of the bench and tied with ropes to the bottom of the bench. My ass was on display and hanging out off of the back of the bench. This provided convenient access to the thin young German woman with spiked silver and pink hair who was fucking my ass. My hands were tied to the bottom on both sides of the bench. A rope was wound across my chest and then around the bench to complete my bondage. This provided convenient access to Lady S who squatted over me and spread her pussy lips inches from my open mouth. Lady G was standing nearby and seemed highly aroused by all the action. Just before Lady S squatted over me, I noticed that Karen and the lovely Lady M were kissing and rubbing their half naked bodies against each. How I got to be in this place at this time and what then happened is an interesting story. Life with Karen, or Tasty as I called her in private, was fantastic. I was continuing my journey to submission. My sexual submission to Karen continued to evolve. She controlled the sexual part of our relationship and we dealt with the rest of our lives as partners. Karen became even more beautiful as she aged. She put a priority on staying in shape and her body remained tight and toned. She has the best ass I ever seen. Karen was a successful attorney and dressed with style and always used lovely fragrances. Her success and style also continued to arouse me. Karen was a really horny woman whose sexual appetite was further stimulated by being in charge of our sex lives. I became the absolutely best pussy licker ever since I had so much practice. Good thing I liked it so much. We were creative in using different positions and places for me to pleasure her. Karen really liked sitting on my face and having my mouth and tongue buried in her pussy. She would order to me to do that many times each week. We'd be sitting around watching a movie and then she would pause it and point to between her legs. I was happy to be there for her in that way. She frequently used her favorite dildo which was one that fit over my chin and allowed my tongue and mouth to caress her clit. She used other dildos in my mouth to fuck herself and ride my face for her pleasure. Karen did like to spank me and most of our sexual times together began with a hard spanking to arouse her and put me in my place. She would occasionally fuck my ass with her strap-on. She usually kept me in chastity to build up my sexual appetite. I would wear the chastity device under my business clothes. We continued to play with her Mom and Lady Elena but that is a story for another day. Life was really good. However, there are always challenges in any relationship. It is especially hard to maintain the freshness and intensity over the years. We both really tried hard to keep the sexual energy growing. We experimented with several kinky activities. We especially enjoyed sex in public. We went to clubs and would sneak into public places to have sex where could have been exposed. We were careful not be stupid and it was a real turn on. We especially liked to go out to secluded places in parks and very late on summer nights to our suburban yard. Karen would pull up her short dress and I would devour her naked pussy. It was challenging for her not to moan too loud as I made her cum. Not having kids made it easier for us to enjoy these kinky adventures. You may be one of those rare guys would can get and stay hard after age 50. Good for you. I found that my erections were not as frequent or as hard. They also did not seem to last as long. Wish I was twenty again and could get hard and get off several times a day. This bothered me and really bothered Karen. She enjoyed cock. She was always on top when we fucked unless there was someone else, mostly her mother, who fucked me in the ass as I fucked her. I knew my declining erections was a problem since she often expressed her frustration. Karen mentioned making me a cuckold so that she can get satisfied with cock whenever she wanted. I knew she could decide to do that at anytime but I expressed to her my concern that I might lose her. Karen was reluctant to proceed until I was ready. My sexual submissive to her was only one part of our life together. We enjoyed a strong bond and both wanted that to continue. We kept talking about it and Karen did more thinking and research. We both loved to travel and our travel and sexual needs came together. Karen found out that Berlin was the fetish capital of the world. Some may disagree but I did find it to be an amazing city for those who walk on the kinky side of life. There are many BDSM clubs where people can openly explore all their passions. People are able to pretty much do as they please. Karen went online and talked to several other ladies who enjoyed dominating their men. She built a close connection with one lady in particular. She is the lovely Lady M. Lady M is in her late thirties and is a lifestyle professional Domme. She is gorgeous with big blue eyes and a strong shapely body. Think of Heather Graham. Lady M is one of those rare professionals who really enjoys what she does and cares deeply about those who are fortunate enough to be taken by her. She has both male and female submissives who are ready to be there to fulfill whatever needs she has. She has several clients with whom she built a strong relationship. Karen and Lady M talked many times and built a strong connection due to their common interests and outlook on life. Karen talked with Lady M about how she wanted to proceed in our relationship and they developed a plan. We talked it over and I understood and embraced it. We were continuing our journey together. That is how I found myself naked on a bench in Berlin with four other women and Karen. And this was only the first part of all that we were going to experience in Berlin. We met Lady M the first night we were in Berlin to get to know each other in person and firm up our plans. The next day seemed to take forever. Karen and I enjoyed the sights of Berlin but we were always counting down the hours to the evening festivities. During the day we shopped at a very well stocked fetish store. We added many devices to our personal collection and a few items to be used during this trip. When we got back to the hotel my ass was prepared properly for the evening activates. This included inserting a large butt plug a few hours before our appointment with Lady M. I definitely felt the butt plug more as the lube gradually dried out. I mentioned that to Karen who just smiled at my predicament. Finally it was time to arrive at Lady M's studio. She greeted us in the hallway. She and Karen hugged and I was ordered to immediately strip. Lady M bent me over and examined the butt plug. They left me in that position as they went into the living room. The living room doors were closed but when they opened I heard some conversation and the clinking of glasses. Lady M returned after several minutes with a strong pink cord. She told me to straighten up and spread my legs. Lady M tied the cord tightly around the base of my cock and separated my balls. She tied it tightly with a loop on the tip of my cock and used the loop to attach it to a leash. She tied my hands behind my back and told me not to talk unless I was asked a question. She then led me by my aching cock into her living room. Lady M announced something in German as she brought me into the room. I took it to mean that the evenings entertainment had arrived, and that it was me! Lady M led me to the center of the room and the ladies gathered around. She stood next to Karen. Lady M spoke for awhile in German and the ladies smiled and laughed. For the benefit of Karen and I, Lady M then spoke to us in English. She introduced me first to Lady S. (They used names but it is not right for me to use them here). Lady S was also a professional Domme who was a close friend of Lady M. She was dark and tall. She appeared to be very strong and very sure of herself. Lady G is an older woman who was next introduced to me. Lady M explained that she is a neighbor who recently expressed interest having her own submissive man. This was her first opportunity to see if she wanted to proceed. She was short and had penetrating dark eyes. The remaining lady was simply referred to as O. She was the only one besides me who was naked. She was young, very thin and had spiked silver and pink hair. She had really small breasts with large nipples. I found out later that she was Lady M's cousin and a very free spirit. She seemed hyper active. She also wore a very long red strap-on. Lady M smiled at her and said how much O loved to fuck her men. So there we were. My hands were untied. Lady M bent me over in front of the ladies and displayed the butt plug which was deep in my ass. Karen spread my cheeks for the ladies to have a closer view. I heard talk in German which I could not understand. Lady M grabbed the base of the plug and pulled it out. It hurt. She then said that I was very clean and ready to be used as their mouth slut and anal whore. I was placed on the low bench as I previously described. I was on my back with my exposed ass hanging out over one end for their pleasure and my mouth was available at the other end for their pleasure. O immediately strode up to me and to take my ass. Lady M told her to use lub and she put some on her large cock. O grabbed my legs and pointed the cock towards my hole. She guided her cock to my opening and pushed it all the way with one stroke. Her cock was not thicker than I had taken before and my ass was well prepared from the butt plug but it still really hurt. The cock was longer than I had ever taken and I felt it so deep inside of me. O immediately seemed to go into a trance and pounded away at my ass. It was like she was a fucking machine and moaned deeply as she entered me all the way to the base of her cock. She would pull it all the way out and bury it again as deep as it could go. Lady S and Lady G moved to the top of the bench. Lady S stretched one of her long legs over the side of the bench and hiked up her short shirt. Her bald pussy was above my mouth. She told me that she knew I was a piss slut and how fortunate it was for me that she saved her piss. Her English was heavily accented but I understood everything she said. Lady G seemed entranced by the action. She stood close and looked intensely at what O and Lady S were doing. Karen and Lady M stood to the side and had their arms around each other. Lady M stroked Karen's face and told her how lovely she was. She then placed her mouth over Karen's and they both kissed deeply. Karen had occasionally been with other women but she had to be in the right frame of mind. Tonight was one of those times. Lady S spread her pussy lips and placed them over my open mouth. A stream of hot piss soon filled my mouth. She stopped her stream and ordered me to swallow. I had not taken piss for quite some time. Karen thought piss play was gross and we never did it. Her mother enjoyed it but it had been a long time since that happened. I enjoy taking piss. It puts me in the right frame of mind by feeling so used and degraded. Lady S filled my mouth five times. Some piss splashed over my face and on to the plastic mat on the floor. When Lady S finished pissing she placed her pussy on my mouth for me to clean her off. My tongue entered deep into her pussy and she grabbed the my hair as she rode my face. O kept pounding away at my ass while I heard Karen and Lady M moaning with delight. I brought Lady S to her climax and swallowed all of her juices. She stood up and then slapped my face hard. She told me my performance was acceptable but that I could do better. She mentioned something to Lady G in German. Lady G then bent over me and looked me deep in the eyes. I saw passion and curiosity. She stood back and hiked up her long skirt. Lady S helped her step over me and be comfortably positioned with her legs on each side of me. O was humming as she continued her long strokes deep in my ass. I was in subspace and all around me everything was just right. Lady G had a very hairy pussy and soon began to piss on my face. My mouth was not open so most of the piss splashed over my face and on to the floor. I managed to swallow some of it. Lady G moaned deeply and then settled her wet pussy on to my mouth. I stuck out my tongue to be inside of her and used my lips to caress her clit. She moaned deeply as she moved around my face. She came with a strong shutter and Lady S held on to her so she did not fall to the floor. Lady G eventually stood up with a big smile and said something in German to Lady S and they both laughed. I then looked over and saw Karen was eating Lady M's pussy. Lady M sat on the couch and Karen knelt in front of her. Lady M caressed Karen's hair and told her what I wonderful job she was doing. Lady S then went over to O and told her that it was now her turn. O immediately pulled out. O removed her strap-on and strode over to the top of the bench. She immediately straddled me and faced the other end of the bench. She said something in German to Lady S who then told me that my tongue was to remain in O's ass and that I must not touch her pussy. O then bent over me with her hands on the side of the bench near my knees. I directed my tongue into her ass and I fucked her ass with my tongue. I felt O then untie the cord at the tip of my aching cock. That only felt good for a moment as then she took the tip of my cock between her teeth and bit it. She bit softly at first and then harder. She matched the harder bites with my tongue being deeper in her ass. Lady S had put on her strap-on and entered me. It was incredibly intense. I heard O cum and then Lady M let out a loud moaning sound as she came. And so it continued. Lady G tried the strap-on after Lady S but said it was not for her. She really liked using my mouth and wanted to try whipping my ass. She did that several days later and enjoyed it immensely. Lady S made me lick her again to her second climax. O sat quietly on the couch after I made her cum with my tongue in her ass. Lady M and Karen switched positions and I soon heard Karen's climax. Lady S and Lady G eventually left. O curled up on the couch and seemed to fall asleep. Lady M untied me from the bench but retied the cord to the tip of my cock. I was told to sit on the floor with my back against the couch after the butt plug was reinserted. Lady M glanced over at the clock and told Karen that her Rolf would be here in a few minutes. Karen smiled with a look of complete contentment and erotic anticipation. I was drained and nervous but ready for the next step of our journey. TO BE CONTINUED My Journey to Submission Pt. 09b This is another chapter in my continuing journey to submission. This story takes place right away Part 9A. I suggest you the previous chapter to better understand the people and how we got to this part of my story. ***** Karen rose after Lady M said that her Rolf would soon arrive. She came towards me and I stood up. Karen looked me deep in my eyes. She told me about her excitement as were about to begin the second part of the evening. We planned out these adventures and I knew she was so looking forward to her time with Rolf. Lady M came over with a red ball gag in her hand. Karen hugged me and told me how much she loved me. I told her that I loved her too. She gave me a curious smile and told me that the rest of the night will be something we would always remember. She told me that she gave Lady M complete control over me and that I should obey her orders as if they came from her. I knew Karen had discussed everything in advance with her. I wasn't sure exactly what she meant but I thought it was going to be quite an erotic adventure. Karen left to get ready for the rest of the evening. Lady M came closer to me and told me to open my mouth. I did as instructed and she tied the red ball gag in my mouth. The butt plug deep in my battered ass still really hurt after the hard fucking I had just received from the ladies who had now left. Lady M told me that she thought that people listened a lot better when they can't talk and that we had some important things to talk about. She then tied the ball gag and attached the leash to the rope that was tied tightly around my aching cock. She said nothing else as she led away. We climbed a staircase and entered a long hallway. I had to move quickly to keep up with her aggressive stride. We went into the last door on the right. This was her playroom and it was impressive. One wall had a massive amount of BDSM equipment and devices which were neatly displayed. There were whips, paddles, canes, butt plugs, dildos and many things which I had never seen. There was a large king sized bed with chains tied to supports around the entire bed. A large wooden stockade was prominently displayed facing the side of the bed. It looked like one of those that might have been used in midevel times. Lady M led me directly to the stockade. She folded back the large wooden half board to display the wrist and neck locks. Lady M placed leather cuffs on my arms and legs and ordered me to position myself in the stock. She attached my wrist cuffs to hooks imbedded in the stock. She bent my head down and then closed and locked the wooden device. My arms and head was completely bound. Lady M then told me to spread my legs to the base at the bottom of the stockade. She untied the rope constricting my balls and cock and then attached my ankle cuffs to the hooks. I was completely immobilized and bent facing forward. She slapped me hard in the face and went behind me to grab some other devices. I could not see what she was doing but I heard her remove something from the wall display. I next felt Lady M grab the base of my cock and balls and pull them roughly through my open legs to be positioned behind my ass. This was an unnatural position and it hurt. She then tightly squeezed above my balls which made them hurt even more. I then felt her release one of her hands and place a wooden device next to my ass. She further pulled my cock and balls. I soon felt a wooden device be clamped between my ass and my cock and balls. I now knew she had placed me in a humbler. I recall I saw that device in a bondage catalogue. Karen had suggested we get one and I was not too keen on that idea. It hurt like hell. My balls and cock were squeezed painfully behind my ass. It also put my cock and balls in a very vulnerable situation. I moaned deeply into my ball gag and the plug in my ass hurt even more. Lady M circled around to be in front of me. She looked pleased and I could see her arousal. She asked if she had my complete attention. I could only moan and tried to beg her to remove the humbler. Her eyes showed how much my pain aroused her. She told me to take the pain for her. I understood what she was saying. She then pulled up a nearby chair and opened her legs to display her excited pussy. She used her finger to caress her clit and then wiped her finger under my nose. I so wanted to lick her pussy and she told me she knew I wanted her but that would have to wait since we had so much to do. I recall very clearly what Lady M then told me. She said she had come to really adore Karen and that she wanted to help our relationship. She said we had such a deep love and brought out such passion in each other. She said how people crave initimacy and how fortunate we were. She said the relationship between Karen and I was very special and that it must be nurtured to continue strong. Her opinion was that I had wandered away from being a real and true submissive. I was going through the motions and doing what excited me the most. A true submissive wants and needs to serve his Mistress as she desires, not through only what turns him on at the moment. She said Karen had expressed her frustration but did not know how to proceed. She said they discussed the solution she proposed and Karen asked her to proceed. Lady M said she knew the humbler was a lot for me to take and that there would be a lot more. She said she would soon be caning my defenseless balls and cock. She wants to do that because me taking the pain for her aroused her and that I needed to learn that this was for the benefit of the Mistress and not the sub. Lady M grabbed the side of my face and looked deeply into my eyes. She said that the only thing I could decide was whether or not I wanted to proceed. We are in a consensual relationship and that I could always choose not to offer myself to her. If I choose not to proceed then I would be untied and would leave her studio. Karen would go on with the rest of her evening. She also said she knew how much this would disappoint Karen and that I would have to deal with her afterwards. She pointed the cane to left side of the stock. She told to move my head there if I wanted to proceed and to the other side if I do not want to submit to her desires. I knew that I must agree to proceed. I wanted to go forward on my journey to submission. I loved Karen and I knew that Lady M and Karen were correct. My intensity had wandered over the years. I was more focused on my needs and not the needs of Karen. I recalled how I felt those many years ago when I was first trained by Kitty, Karen's mom. I opened myself up to whatever Karen's mom wanted since I needed to please her. I had to earn the right to be with her. I truly understood and moved my head to the left to offer myself to whatever Lady M and Karen had planned for me. Lady M smiled and said was so glad since Karen and I had something special and that she really wanted me to take the pain for her. Lady M rose and walked behind me. Not being able to see her increased my concern and anticipation. She grabbed my balls and then rested her cane on them. I heard her pause and take a deep breath. She then very slowly raised the cane and brought it down softly on my vulnerable balls. She tapped my balls and continued to softly tap them with the cane on the same spot. The pain started slowly and then really built. The repeated motion, although it was relatively soft, continued to build to increasing pain. She would not stop. I began moaning and crying which seemed to arouse her more as I heard her moans. After a long time she stopped the caning and squeezed my balls even tighter. Lady M then grabbed my defenseless cock and did the seem thing to the middle of my cock. It hurt like hell. Once again the gentle taps on the same spot built up to an incredible intensity. I was thrashing and moaning but could do nothing but take it. I had to surrender and soon felt the passion of subspace as time seemed to stand still. I was so in the moment. Lady M then paused and moved on to cane the very tip of my cock. This did hurt the most but I was in another world. I closed my eyes and focused on Lady M's growing pleasure. I was taking the pain for her. I drifted off. The next thing I knew was Lady M kissing my forehead and telling me how pleased she was. She moved the chair closer to me and stood on it. Her wet and excited pussy was next to my ball gag. She reached around my neck and undid the ball gag. She pressed her wanting pussy next to my mouth. My tongue sought her and I fucked her pussy as much I could with my tongue. She moaned deeply. I then caressed her clit between my tongue and upper lips and soon felt her shudder and release all her juices into my mouth. I savored the moment and then heard the door bell ring. Lady M backed away and told me that I was doing very well. I could not speak as I watched her leave the room to answer the door bell. I was lost in my revelry and pain. I heard noises and then the door opened and Lady M walked in followed by a large human being. Rolf was big. Big in many ways. He was tall, about six foot four. He was completely naked. He had broad shoulders and strong tree like legs. Rolf had long blond hair then was cut close on the sides and hung down his back. He also had a big smile. He saw me in my very uncomfortable position. He said something in German to Lady M who told me that he recalled being in the identical situation. She also said he was glad to be him and not me at this moment. Lady pointed to bed and Rolf was placed on his back and his arms and legs were secured. His cock was huge. It was now fully erect and looked like someones arm. It must have been at least twelve inches long and very thick. Lady M whispered something in his ear and kissed his lips. She then rose and left the room. In a few minutes I heard the door open and looked up. Lady M walked in followed by Karen. I can say without hesitation that I never saw Karen look and be more beautiful. She wore a sheer lavender nightgown that barely went past her waist. Her large breasts and erect nipples were very apparent through the sheer material. Her look was one of great intensity and anticipation. She saw Rolf naked on the bed and put a hand over her mouth when she saw his huge erect cock. Karen and Lady whispered something to each other and hugged closely. Karen's eyes then looked over to me and she blew me a kiss and mouthed that she loved me. I knew exactly what she meant. Karen then strode aggressively to the bed and sat on Rolf's stomach. Her hand reached behind and she stroked his powerful legs as she looked him in his eyes. She moved her hips around his stomach. She then reached forward to touch his massive arms and chest. She then bent over and kissed his forehead. She gave me one more look and grabbed the hem of her nightgown and raised it over her head and tossed it aside. Karen then moved lower on Rolf and raised her hips. She grinded her pussy into his massive cock. She started to moan deeply. Lady M was watching intently from the side of the bed. I could feel her arousal. My balls and cock continued to ache but I was focused on Karen and her great enjoyment. Karen lifted up again and grabbed Rolf's huge cock and placed the tip against her ready pussy. She gasped as the tip of his cock entered her. She paused and savored the moment and then slowly lowered himself on his massive cock. Rolf remained perfectly still and focused on Karen's lovely face. Karen moaned even more as gradually took all of his cock into her pussy. She shouted as her pussy took in his entire cock and she rested on the base of his balls. She shouted out that this was fucking amazing. Lady M stood closer to me and told me that this is what Karen needed. A real cock deep in her from a sub who has been trained to not cum until ordered to do so. Karen closed her eyes and slowly fucked herself with Rolf's cock. I could see her bliss. She was totally enjoying every inch of his cock. It then became completely quiet as Karen gradually took in every inch of massive cock. She began to scream as she came. She violently gyrated up and down and I took in her total bliss. Lady M gasped and started to finger her own clit. Karen rested on his massive cock and seemed to gather herself as she let the ripples of her massive orgasm go through her. After a pause she looked over to Lady M and said thank you. She then looked at Rolf and smiled leeringly at him. He said something in German that showed he was also pleased with her joy. Karen then asked Lady M if Rolf would now be able to cum. Lady M held up her hand and asked to pause for a moment. Lady M then bent over to talk to me. Lady M's eyes glistened as bent towards me. She then told me that I now had another decision to make. She said she would soon instruct her sub Rolf to cum deeply inside of Karen and I would then lick it all out of Karen and then clean Rolf. She said she knew that was a big step for me as I had previously refused to do anything with men or their cum. She told me this is what Karen wants me to do to show her my devotion. I could decline and then I would be released. She said she knew this would greatly disappoint Karen and then I would have to try to work this out with her. It was then all so clear to me. I knew that I wanted to show my devotion to Karen. I loved her and I now understood that it was all about her pleasure and not what I felt like doing. I told Lady M and Karen that I would willingly do whatever they desire. Lady M stroked my face and told me that Karen and I very fortunate to have each other. Karen looked over as she rested on Rolf's cock. She told me that she loved me and that she was so pleased. Lady M then left me and went to Rolf and told him he could come when instructed to by Karen. Karen then rose up to the tip of his massive cock and slowly lowered herself on it. Lady M stood close to the bed and I could see the deep affection between Lady M and Rolf. Karen soon showed her arousal by moaning after she once again fully implanted herself with Rolf's massive cock. I heard Rolf moan as Karen expertly caressed his cock. I knew Karen had a strong pussy muscles as she did exercises to keep all of her muscles strong. Rolf soon started to gasp. Lady M reminded him not to cum until given permission. I could tell he was struggling. Karen did not seem to notice as she was completely enjoying the second fucking. Karen kept slowly rising and lowering herself on his cock. Rolf continued to struggle. Karen then let out a deeper moan. She looked at Rolf and told him that he was to cum with her. The relief on his large face was clear. Karen start to cum again and Rolf then raised his ass to lift Karen up and down as they fucked with greater abandon. Karen grabbed his chest for support and soon I hear his grunts as he released his load deep in Karen's pussy. They eventually settled down and Lady M went behind me. She undid the clamps on my wrists and legs and then raised the wooden stock to release me. The humbler was still on me so it was hard to move. Lady M told me that I must deal with it. The humbler was a reminder that I am doing this for the pleasure of my Mistress. I could not stand up without painfully pulling my balls. I somehow managed to shuffle over to the bed. Karen had rose off of Rolf and was laying next to him on her back. I went to the foot of the bed and Karen opened her legs and pointed at her pussy. Her look of passion and satisfaction was one that I will never forget. I immediately crawled on my knees to be between her legs and smelled the pungent odor of Karen's pussy and Rolf's cum. I paused and looked up at her. I told her that I loved her and that I was hers. She reached down her hand to grab my head and told me that she knew and that I was to get busy. I stuck my tongue deep into Karen's pussy and began lapping all the juices. I could taste the sweet saltiness which must have been Rolf's cum. I just kept doing it and appreciated Karen's moans and encouragement. After a long time she lifted my head and told me I was finished cleaning her up and that now it was Rolf's turn. I knew this would be the hardest part for me. I had never sucked a cock. Something about it had always bothered me. I pushed aside my concerns and immediately did it before I could think some more. It was fine. His cock was mostly flaccid but was still huge. I took his cock in my mouth and just started sucking. I was so aroused and I saw how intently Karen was watching. Rolf seemed to enjoy it and encouraged me. My mouth started to ache and then after awhile Karen told me that Rolf was now clean and that I could stop. She motioned me to come forward and our mouths paused next to each other. Karen never wanted us to kiss after I ate her pussy so I was not sure what to do. Karen took control and pressed our mouths together. We kissed deeply and passionately. And yet this was only one of many parts of our activities in Berlin. I savored the moment as I layed next to Karen. Lady M layed next to Rolf and we all talked over the experiences we had all just shared. I asked Lady M if she could remove her humbler. She laughed and said that this humbler was a gift given by her to Karen and that Karen would decide when to remove it. Karen smiled and said that it would now be removed as a reward for me being so fantastic. We then kissed again deeply. To Be Continued as Parts 10A and 10B.