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Raised a Sissy Alessandra Durante I've been a sissy my whole life. I didn't know that when I was child, but that what I was raised and reared to be. I never had a choice in the matter. I was born into a wealthy family, but I never knew the privileges of wealth. My mother was a strong willed woman who ran our countryside home like a queen. My sissy father was her faithful and humble servant. My father doted on her and obeyed her every command as if he had no choice. My father's lifestyle was forced on me from a young age. I was born to be his assistant. I was the junior maid according to my mother. I heard that term my whole childhood as I followed my father around as he worked around the house, provide whatever assistance I could in my maid's uniform, tights and one-inch heeled shoes. I never had the choice to not be one of the help. As long as I can remember, I've been in uniform just like my father. I was even named in his honor. My father was known as Priscilla, while the given name on my birth certificate read Prissy. I believe my name was meant to symbolize my place in the family. I felt that it made me seem like I was a lesser version of my sissy father who was always going to be the family's senior maid as long as he was around. My father helped me growing up. He taught me how to serve women and home schooled me as required by the State. He was a good teacher, even though he was aloof with me. Occasionally, I almost as if he didn't consider me good enough to receive his attention. My older sister, Miss Tiffany, was the apple of my mother's eye. While I was named for my sissy maid father, Miss Tiffany was named for something beautiful, fragile that was to be cherished. She was the princess of the house to my mother's queen. From a young age I was lead to believe that my father and I solely existed to serve the two of them. It was our purpose in life as lesser beings. Even though we were never called sissies when I was young, I knew that we were different from my mother and sister and the female friends of my mother that sometimes visited us. It was not simply our uniforms that made us different. We were always told that we were less than women. My mother and sister never called us sissies and they certainly never called us men when I was a child. We were spoken of as things. We were their servile pets. It was their gender that made them worthy of our devotion, my father explained once to me. My sister, mother and my mother's friends were all of that same opinion, which was driven home to me since I can first remember. Women are sacred, and people like my father and myself exist to please them. I remember my mother explaining to me when I was five that feminineness is godliness. Those not blessed with femininity were forced to serve at the altar of the sacred female. I was told that women were served because they were beauty itself, while we served them because we were ugly womanoids. We were beneath them in every way and had to be treated as such. Our subservient positions were why we both had to call my sister Miss Tiffany. While my sister was permitted to call my mother Mommy, I was restricted to calling her Mother, but never in the company of guests, while my father had to call her Madame. Miss Tiffany and I were both permitted to call our father by his first name. While I respected my father, my sister was raised to believe that, like me, he was beneath her. Respect in our household was expected to be a one way street. We respected the women we existed to serve, but they only looked down on us. For the first five years of my life, I thought that this was the natural order of things. I had never met what I was later told were men. The concept of a non-woman wearing pants was alien to me. The very idea of a non-woman not wearing a skirt or dress so he could curtsey to superior beings never crossed my mind. That all changed when my sister got back from first year at boarding school. She regaled us all with tales of men wearing pants and not curtseying to her. She was not surprised by this since my mother had explained it to her before she left. I was not privy to that conversation, so Miss Tiffany's words struck me as something queer. I asked permission to ask my mother a question about these 'men' and 'boys' that my sister mentioned. I asked if they were like me. Miss Tiffany and mother broke into laughter as my father smiled a little. My mother assured me that they were nothing like me before my sister called me a word I never heard before. She said I was a sissy. I was told that sissies were men who dressed in clothing that women were expected to wear and served women or other men. For the first time in my life, I realized that I was a freak. I was devastated by what I was hearing. At that moment, I spoke out of turn. I could never remember speaking in the presence of my mother or Miss Tiffany without their permission before that. I asserted that I wanted to be a man. My mother and sister broke into laughter once more. I turned to my father and saw no help was coming from him. When my mother stopped laughing, she explained that being a sissy was not a choice. She said that some people are just born to be sissies. I accepted that explanation at the time. I was still a child, and I figured that my mother was not lying to me. Not long after my sister went back to boarding school, I saw a man for the first time. I later learned that my mother had been seeing men for years during her trips to the city. However, given that I learned of the existence of men, my mother no longer felt the need to keep them away from our family by traveling to the city to see. Instead, she decided that they could now come to see her. Several men would come by over the years to spend many nights with my mother. The faces changed, but not the look in their eyes. They all had the same scorn for my father. I would hear the remarks about her sissy husband. They were more conflicted about me. Some saw me as her sissy son, but others felt that I might have been forced into it. They figured that I didn't have the choice they assumed my father had. Given my upbringing, I'll never know which view was right. I am a sissy, but I never had the choice to not be one. I don't know if I was born one or whether it was the result of how I was raised. That fact will haunt me forever. With the exception of my increasingly complicated school work, cosmetology lessons and chores around the home, not much in my life changed until I was 13. I was helping my father clean up the house when he asked me to help him lift a table that he always had trouble with. He never was able to do it alone. I walked over to the table as he grabbed the cleaner and found that I was able to move it. I lifted it from the ground and moved it so my father could clean beneath it. Priscilla looked at me with a slacked jaw. I was startled by the look he gave me. He quickly put down the cleaner and walked away to talk to my mother. My mother came back into the room carrying two fifteen pounds weights that she exercised with. My father could not lift them off the ground at the same time. She asked me to see if I could. I saw nothing peculiar about the test, so I walked over and picked the weights up off the floor. She nodded to my father and said, "Prissy's coming along nicely." I curtseyed and thanked her for her praise as I always did, not aware that I had done something terrible in her eyes. I didn't realize that until sometime later. The next day I started taking the same pink pill my father took monthly. My mother made me lift that same weight everyday after that for month. At first, I had no problem doing it, but it increasingly grew harder for me to do until I couldn't lift the weights up from the floor. As my first month on the pill ended, I was as weak as my father was. It took me some time to realize that it was the pill that weakened me. I dreamt about being able to cheek it or spit it out, but I never had the chance. I took that pill every week, and my mother inspected my mouth every time to ensure that I swallowed it. I knew she would punish me severally if I tried to not take that pill. I was too weak to do anything about it. I'm sure that keeping me weaker than her and my sister was something she felt was necessary to ensure that I would continue to accept my submissive role in the household. I can't say that I think she was wrong. Soon after, the one inch heeled shoes of my childhood gave way to high heel training. While I was not expected to wear heels at all times, I was expected to learn how to walk in them properly. I was told that I was getting to old to serve guests in flats. Flats were good for every day wear, but my mother stated that she would be embarrassed to have me serve her friends in anything less than 3 inch heeled pumps. I learned to walk in those damn shoes. I fell to my sister's amusement the first time I wore them. I had a hard time learning to walk in them, but my father did his best to show me the proper way to take short steps and properly land my feet. Soon I had progressed enough to serve my mothers friends and lovers in heels. Walking in them became second nature. While they always hurt my feet, ankles and back, given enough time, I was able to manage it. My life as the junior maid continued on without any major changes until I finished my formal in home education and passed the state mandated test that made me a high school graduate. That only resulted in freeing up more time for me to work around the house. By that time, I figured I would never know a life any different from the life I had lived to that point. Shortly after my eighteenth birthday, however, my mother told me that we were taking a trip to see her friend, Miss Denise. I was excited because I had never left the grounds of our home since I was a young child. I was intrigued about seeing what lay beyond the gates of our twelve acre property. I had known Miss Denise all of my life. She came by to visit every summer when she needed a break from her family. I knew she was married and from what I understood, she had the same sort of marriage that my parents did. My father and I packed up the car for the trip, and we made the five hour drive. When we arrived, my mother and sister went to the door first and were greeted by Miss Denise. She motioned for me and my father to come up to the door before we grabbed the bags. We curtseyed to her before we were allowed inside. I walked into the large home that clearly dated to the beginning of the 20th Century and saw a fit, light skinned woman in her early twenties walking towards the door with a smile on her face. "This must be the young sissy I've heard so much about", she said. Miss Denise smiled and said, "Yes, this is Prissy. Prissy, I'd like you to meet my daughter, Tess." "It's nice to meet you, Miss Tess", I replied with a curtsey towards the tall, crimson haired girl. She smiled and nodded and said she was happy to meet me as I heard a ruckus behind her. Three sissies in identical pink and white maid's uniforms came out. I gawked at them for a moment as they approached us. I assumed they were their dress uniforms because they were wearing white tights and pink, four inch heeled pumps decorated with large white bows on the vamps. My father and I only wore white tights and heels to serve company. Heels make cleaning too difficult and dark colored tights or stockings or nude pantyhose was better for cleaning because they did not appear as dirty as light, solid colored tights did after a little cleaning. I felt a little underdressed in my grey and white maids uniform, nude pantyhose and black flats. Miss Denise smiled at the sissies and said, "I want to introduce you all to my three sissy sons, Bunny, Missy and Pansy." The three boys blushed before they curtseyed for my mother and sister. I looked at my sister's face and saw a grin on it. She liked seeing other sissies like me. She was only 20 years old, but she was already tired of men. She had told me that they were too difficult to keep around for long and were only good for one thing anyway. Although, I knew better than to ask my sister personal questions, I knew what she was referring to. Miss Denise than called out to her husband. I saw a sissy around my father's age come mincing into the room. He brushed his dainty hands on his frilly apron as he walked over and curtseyed to my mother, sister, Miss Denise and his daughter. Miss Denise then said, "Priscilla, I'm sure you remember my husband, Kitty." My father beamed and nodded before he hugged Kitty with a smile on his face. I had never seen my father give that type of affection towards anyone. He was always meek around Miss Tiffany, my mother and her friends and was always kind of reluctant to share his feelings with me. When I was younger, I thought he was disappointed in me, but as I grew older I came to believe he was ashamed of himself because of the life he had thrust upon me to satisfy his own desires. On Miss Denise's orders, the sissies took in our bags and led us to our rooms. My mother and sister were staying in the two guest room while my father and I were going to stay in the maid's quarters in the attic. We walked up the servant's staircase in the kitchen to the upstairs before we ascended the hidden stairs case that led to our quarters. There was a small bathroom at the top of the stairs and a common area with a table, chairs and a kitchenette. There were two rooms on either side of the common area. My father followed Kitty into his bedroom, while I was led by Bunny into the bedroom he shared with his sissy brothers. I was shocked to see only one bed in the room, which was queen-sized. Bunny explained that the three sissies shared the bed in addition to the room. I had never shared a bed with anyone so I was a bit concerned how I would do sleeping with three other sissies. I looked around the room and saw only one other piece of furniture. It was a large white dresser with a vanity on top of it. Bunny explained, "We don't have much furniture because we only have five different uniforms." I nodded as Bunny started unpacking my bags into the dresser and the closet that was full of nothing but uniforms and shoes. I was aghast to see not one pair of flats in the closet. I realized that these sissies only wore heels. Having noticed that the house looked spotless, I feared that my mother would get ideas from watching Miss Denise's sissies. I figured that my mother could easily conclude that if these sissies could do such great work in heels, my father and I could do so as well. When we finished packing away my clothes, we headed back down the stairs and into the kitchen where we were joined by my father, Kitty, Missy and Pansy. Kitty gave us Miss Denise's orders, and we made lunch for the girls before we carried it out. I noticed that when they finished serving Miss Denise and her daughter, the sissies always stood with their heads down as they held hands. I found it odd and wanted to ask why they did it, but it was not my place. I kind of felt jealous of them too. While I assumed I had the same upbringing as them, I figured that at least they had someone else to talk to who was going through the same thing. I thought they were lucky to have each other for support. I was surprised by the way Miss Denise had us work at the lunch. Bunny, Missy, Pansy and I were each called forward separately to serve the girls at different intervals. I felt a little nervous being watched by Miss Denise's beautiful daughter. She even looked my way when I was not serving her. I would catch her starring before I would dart my eyes towards the floor, fearful of her catching me looking her in the eye. After lunch, Miss Denise suggested a trip on the family yacht. My mother agreed and the sissies practically shoved me and my father into the kitchen before we rushed up to the servant's quarters. I went back into the junior sissies' room and watched as they took out their special uniforms for boat trips. I looked at the uniform that Bunny was trying to give to me. He smiled and said, "It's one of my spares, so I think it's the closest fit for you." I smiled and nodded at the sissy as it took the uniform from his slender fingers and took off my maid's uniform. I slipped on the uniform and stared down at my body beneath it before I caught my reflection in the mirror. The uniform was something far different than I had worn before. The hemline was much shorter than any of my uniforms. The uniform consisted of a white mini dress with ruffle skirt with a flap collar that was adorned with red anchor symbols on both flaps. It had blue tie front at the bust and a blue sash running across the waist as well as blue trim on the sleeves and skirt. There was also a large attached red bow that rested over my rear. I looked at my reflection in the mirror and was embarrassed by what I was wearing for the first time in my life. While I knew that I should have been embarrassed with myself for wearing anything feminine at all, this uniform was more immodest than anything I had ever put on. I had only seen something like it worn on Halloween when my sister sent back pictures from a high school party she went to after sneaking away from her boarding school. Pansy came over to me and noticed my unease. He smiled and kissed my cheek. I was surprised by his act since I had never been kissed before. I looked into Pansy's affectionate eyes as he said, "Don't worry, we're wearing just like you. You look great in it too. I'm so jealous of your legs." I blushed at the sweet sissy's praise before he placed the matching white and blue trimmed sailor hat on my head. I felt ridiculous wearing it, but I was not one to question a woman's authority or judgment. I put on the matching white gloves before the sissies brought out the red patent leather heels that went with the uniform. Bunny and Missy's shoes were one size to big for me, so I had to wear Pansy's, which were a half size too small. They pinched my feet as I walked behind the sissies as we headed down the stairs. My mother and sister grinned at me as they saw us dressed in our uniforms. "Now, these are fine sissies", my sister said to Miss Denise. She nodded and said, "I take great pride in their appearance, and they do as well. Though I must say, Prissy is quite fetching in that uniform. Why don't you girls let him show off his legs more often?" My sister seconded her statement, but mother shrugged it off as we walked behind them to the boat. I didn't see my father around as we boarded. I found it quite difficult to step onto the lazily drifting boat that rocked as I stepped onto it. The discomfort and imbalance I felt in my feet made the task quite arduous for me. The women took seats on the back of the boat in the sun as they asked us to go into the cabin and bring them the drinks and appetizers that Miss Denise's sissies had stocked the boat with before our arrival. As I carried out a plate of appetizers for the women, I caught site of my father and Kitty walking towards the boat. They came out dressed in their white tights and blue high heels that were patterned with white trim, a white bow and decorated with a red anchor at the vamp. Their uniform was more modest than ours, with a lower hemline and a red petty coat beneath the blue dress. As my father and Kitty steered the boat around the sea, I walked around freshening up the girls' drinks and bringing them whatever they requested. I saw Tess's eyes upon me as I walked around. As I walked away from her after bringing her a drink, I felt her hand come under my skirt and squeeze my ass. I felt a bit embarrassed, but her touch excited me. I had never been touched so intimately before in my life. It was a strange feeling that I wanted more of. The thought of being caressed like my mother was by her lovers or my sister was by hers excited me. The thought kept coming back into my mind as I continued serving the girls while trying to keep my balance in my heels. However, I knew that eventually I'd slip up. Sure enough, I did, and I dropped a drink onto the boat's floor as I fell face first to the floor. I was happy the drink fell to the side of me. I wouldn't have been able to forgive myself if I stained Bunny's uniform. Bunny and Pansy helped me to my feet as the women laughed at my clumsiness. "I apologize for Prissy. This is her first time on a boat, she doesn't have sea legs", my mother said to Miss Denise. She smirked and said, "She'll learn." I wondered what she meant, but I didn't have time to think. I had to clean up the mess I made and get back to serving the women. We went back to Miss Denise's home after we helped tie up the boat. We went into the kitchen and began making the girls their dinner. Kitty took a special interest in me and showed me in detail how he prepared his daughter's favorite meal. I watched intently and helped him as best I could while we all followed his instructions. When the dinner was finished, we carried it out and served the girls just as we served them lunch before we were permitted to pick upon their leftovers in the kitchen. When we finished, Miss Denise ordered us to retire to our chambers for the night. Only my father and Kitty were permitted to remain up with the women. I felt strange as I headed to bed before eight, but I knew I was guest and had to obey Miss Denise's orders as if they were my mother's or sister's. I was relieved to be able to get out Pansy's heels and rubbed my feet as the sissies got ready for bed. They dressed in identical pink chemises with ruched mesh sides and a lace ruffled hem. The camisole straps were ruched as well. They were still wearing their white tights underneath their chemises as they watched me to see what I was going to wear. I was embarrassed by my relatively drab clothing. It was far less pretty than theirs. I put on my plain black satin chemise and pulled off my tights before I crawled into the bed and was joined by the sissies. I quickly found myself sandwiched between Bunny and Pansy as the cramped bed forced us to sleep on our sides. Bunny's soft arm fell over my side as my own arm went over Pansy who caressed it. I had never slept in a bed with anyone else before. It felt strange, but it felt right. I got excited as I smelt the sissies perfume around me and felt the soft skin of Bunny and Pansy on me. Soon my cock was poking at Pansy's chemise and tights covered ass. He turned his head and smirked at me as he asked if I could control myself. I apologized and said that I would try. As we laid together, Missy asked, "What's Miss Tiffany like?" I shrugged and said, "She's a woman. I obey her. That's really all there is to her." Bunny interjected and said, "Is she kind to you?" "Well, she kind of teases me about being a sissy." "That's normal", Missy replied. I nodded and said, "I guess, but why do you want to know?" That's when I heard the words that rocked me to my core. Bunny answered, "Our mother told us that Miss Tiffany is here to see if any of us are good enough to be her sissy wife." I was shocked to hear that my sister would marry a sissy. She had always dated men, and I figured that she would choose to marry one of those men that she spoke so fondly of and not a sissy like me, who she took so much pleasure in deriding. I answered, "I had no idea. My mother didn't tell me." "She didn't?" Pansy said in near shock. I nodded before Bunny interjected, "Prissy, you're here so that Tess can judge if you're wife material." I was dumbfounded. I shook my head and said, "That can't be." Bunny assured me that it was. The sissies told me that the plan hatched between our mothers and sisters was to trade me for one of the sissies. If Tess found me to be an acceptable sissy husband and my sister deemed one of the sissies good enough for her, I would find myself married to Tess. I wasn't sure how I should feel. I though Tess was beautiful, and I loved it when she touched me on the boat, but I knew I would be separated from my family. I would no longer be with my father or sister and would be serving different people. Given Miss Denise's clothing choices for her sissies, I was a bit concerned with what a life of servitude to her daughter would entail. Still, I figured that it would be nice to have more sissies to support me as I moved on to a new mistress. I told the sissies as much, which prompted a brief silence. Bunny's voice trembled while she told me what would happen to the two sissies that Miss Tiffany didn't pick. Bunny said, "The two of us that Miss Tiffany doesn't choose are going to be offered to Mr. Davenport." Pansy shuddered as he heard Bunny's words. I asked, "Who's Mr. Davenport?" Bunny answered, "He lives down the road. He's a man who likes sissies, even more than our mistresses." "What do you mean?" "He makes us pleasure him when he rents us." I didn't understand what Bunny was getting at, but Missy explained in blunt terms, "He makes us put our lips around his cock." Now, at that point I had never heard about oral sex being performed on a man. I assumed that it was a one-way street like with my parents. My father performed it on my mother, but never vice versa. I couldn't even fathom my mother or sister doing something so degrading as putting a man's cock in their mouth. Bunny continued and said that Mr. Davenport would take only sissy. The other sissy would remain in Miss Denise's home as the junior maid. However, they explained that I would not be living with them. Although I would see the junior maid, I would not be living with either of him. I was told that Miss Denise purchased the home next door for her daughter. I was going to be the sole maid in her household. Kitty was going to help integrate me to the role, but, soon enough, I would be the sole sissy of the household. ----------------------------------------------------------------------- The next morning, the alarm clock went off at six. We stirred out of the bed and dressed in our uniforms and headed to the kitchen. We prepared coffee, tea and scones, as well as biscuits to tide the girls over until they told us what they wanted to breakfast. We ate on our feet as we waited for the girls to get up. The girls got up and ate what we prepared for them before we were told that they wanted eggs and waffles and got to making breakfast for them. I carried out the food with the other junior sissies as our fathers continued slaving in the kitchen. After we cleaned up after breakfast, Miss Denise called us into the parlor. I stood beside Bunny, Pansy and Missy as Miss Denise announced, "I have some joyous news to announce." My stomach sank as I heard her words and knew what she would say next. "Tess has decided that Prissy is sufficient to meet her needs." I looked at my mother and sister who smiled at me before Madame called me towards her. She smiled at me before she reached out and squeezed my testicles through my white tights. I cringed and whimpered a little in her grip before she said, "I think you'll be the perfect sissy maid for me. You know your place in this world is before the delicate feet of a woman. I look forward to taking you as my bride." She released her grip, and I felt a surge of relief and excitement before she stood up and placed a collar around my neck. I went to pull at it, but Madame said, "Don't touch it, Prissy. I expect you to wear that all times. It tells the world that you have an owner. It's your engagement collar. I've got a better one for our wedding, which comes with a lock you can never take off. With the engagement collar, I expect you to withstand the urge to remove it. Do you understand?" I nodded weakly before my mother announced that Miss Tiffany had made a decision regarding the sissies. I watched as Miss Tiffany stood up and walked in front of the sissies. She inspected them from head to toe and spoke in a booming voice about their various flaws. I watched the sissies hang their heads as they heard her cutting words before she smiled and said, "Bunny is my choice." I watched Bunny's eyes light up. He looked relieved and smiled. The looks on Pansy and Missy's faces were the total opposite. They looked to be on the brink of tears as they knew that had a fifty-fifty shot of serving a coarse man instead of a divine female. Pansy and Missy were taken out of the room by our fathers as Bunny and I were allowed to remain with the women to await the seamstress who was coming by to measure us for our wedding gowns. She arrived within 30 minutes of us receiving the news. She measured us both before we were given our next orders. Bunny was told to retire to the porch with Miss Tiffany so they could have some alone time to discuss their new arrangement. I had to accompany Madame to her home next door. I walked slightly behind her as she told me about her new home. She seemed to enjoy showing it off to me before she showed me new quarters, which were spotless. The whole house was immaculate and gave off a sense of power. Only my quarters were furnished cheaply, which was clearly done to appropriately indicate that the room was reserved for someone beneath Madame's station in life. As I served Madame for the first time in her home, I heard a knock upon the door. Madame ordered me to answer it. I was a bit nervous about what to expect, but when I opened the door I saw large man who walked right in. He glared down at me as he said he was there to see Madame. I trembled as the 6'4", broad shouldered man nearly knocked me down as he walked past me. I watched as Madame ran up to him. He picked her up as their lips met. I was jealous of him instantly. I knew I was in the presence of a man. Not only that. He was a man that my spouse to be was clearly infatuated with. I finally knew how my father felt. I was deeply ashamed of myself for letting her share her body with someone other than me, but I knew I could do nothing to stop it. After their embrace ended, Madame called me towards them. She introduced the man to me as Master Thomas, her boyfriend. I curtseyed to the man as I had been trained to do for my mother's lovers. He sneered at me and shook his head. "This is the sissy you're going to marry. Look at him. You're going to marry this thing." My eyes hit the floor as the man disparaged me. "Don't be mean to her, Thomas", Madame spoke up in my defense. I smiled at her as she continued, "If you can't coexist with her, we're done? Got it?" "Why can't you just marry me? I'm a guy! Why would you marry a fag?" "What can you do for me that Prissy can't, except for one thing? She will serve me for the rest of her life. Are you prepared to cook me dinner and take care of my house for the rest of your life." Master Thomas sneered and said, "That's women's work." "No, it's sissies work. That's what Prissy excels at. She's the perfect housewife. If you can get over your sissy phobia, she can serve you too. You can share my body. Prissy can't do that. She can share the rest, but not anything more." "If you marry him, where's does that leave me?" Master Thomas shouted. I never heard someone direct such a tone towards a woman. I started to shake before Madame retorted, "The same place you are now. You're my lover, but you're not useful when it comes to the other important things. Think about it for a minute. You get to fuck me, but he gets to hear about my day, he gets to cook and clean for me. You both get to do the things that you were born to do while gets to what he was made to do." Master Thomas shrugged and said he could accept that, which pleased Madame. He understood why she wanted someone like me around, but he asked, "What's so great about this particular fag?" I hung my head as he pointed at me. Madame answered, "She's a darling little sissy. She's loyal, diligent and knows her place, and look at her. Look at her slender physique and long legs. Any girl would love to have a sissy like her, that's why I'm going to customize her." "Customize?" Master Thomas interjected, asking the very question I wished I had permission to ask. "Yes, I'm going to turn her into someone only I could love. I'm going to fatten her up so bad that no girl would ever want to touch him. I can't wait to see that huge ass and pudgy stomach replacing that waif like frame. She'll have cankles and thunder thighs instead of those model thin legs. She'll be my little loyal sow." I stared down at my thin body and shivered as I thought about what she was planning to do to me. She was going to do her best to make sure that no woman but her would ever want me as her sissy. I went back to her mother's home that afternoon and found that my parents had already packed up for the trip home. Before we got back into the car, my mother gave me a blue pill on Madame's orders. I put it into my mouth and swallowed it without hesitation, even though I'm sure I knew what it would do. We drove back home as I fretted in silence about my future as Madame's sissy bride. I began packing up my belongings with my father shortly after I arrived home. He had no words of advice for me and kept our conversations very formal as he often did. I wondered if he was sad to see me go or had long since concluded that I was nothing more than a junior maid who was beneath him. I got back into my normal routine as I waited to be transported back to Madame's. The only difference was the additional pill I had to take that seemed to slow my metabolism to a crawl as it simultaneously made me hungrier than I had ever been in my life. By the night before I left to return to Madame's, my more form fitting uniforms felt uncomfortably snug on me. That night, before I went to bed my father came into see me. He wished me well and said that he was sure I'd make a great sissy wife. I thanked him for his kind praise, but there was nothing more to be said between us. We had a warm collegial relationship, nothing like what my sister had with my mother. I envied her so much. Not only for being a top our social order, but for the affection she seemed to receive from my mother. It was something my mother could not share with me given my lowly status and it was something my father seemed disinclined to give to me as well. I wish I could say that I thought leaving them behind would be traumatic, but I can't. I was only a servant in that house and never felt the love that my sister received in abundance. The next afternoon, Bunny arrived with Madame and Miss Denise. I asked where Pansy and Missy where and was told that they were left with Mr. Davenport so he could make his final decision regarding which sissy he would purchase from Miss Denise. I helped my father unpack Bunny's belongings and brought them into my old quarters before my own belongings were packed into the car for the ride back to Madame's. I spent the rest of that day serving my mother and sister as the family's junior maid for the last time. I took Bunny with me as I worked that day and showed him where everything was in my house before we retired for the night. I spent my last night in my quarters nuzzled up beside Bunny in my single bed. We talked about what to expect from our sisters, but I found the urge to question our situation. I asked Bunny, "Have you ever wondered why we can't be men?" "No. I know why." "Why? Because sissies can't be men, silly." "But why are we sissies?" "Because our dad's are sissies." "That doesn't mean we have to be sissies. Were their father's sissies?" "I don't know, I try not to dwell on what I can't control."' "I can't stop dwelling on it. Ever since I found out I was going to be traded for you, I just can't help but feel that this isn't how things are supposed to be. I look at the men that have come through this home and think why can't I be like them." "They don't wear uniforms, silly or at least a maid's uniform. Men would never wear such pretty a chemise either. Men are coarse, you're weak and delicate." "I don't want to be weak, I want to be strong. I know men aren't really women's equals, but they're a lot closer than us." "That's true", Bunny replied as she stroked my side before she continued, "but we're not one of them." "Why is that? This is all our father's fault. If they had been men, we wouldn't be in this mess." "It's not that bad of a life. We have someone to serve...." "Yes, we serve them. We have no choice in that matter. Think about that. Men don't serve them. They do other stuff for them, but they have a choice in doing that stuff too. We just blindly follow orders." "It's our place in life", Bunny counseled. "It didn't have to be. If our fathers had just not let themselves be controlled by our mistresses, we would have been raised to be men and not simpering sissies." "Don't dwell on this", Bunny said sadly. "We've all been there before. We can't change the past. I was raised to be a sissy. I'll never unlearn it. I know, no matter how hard I try, I'll never lose my training. Neither will my sissy sisters. Neither will you. You were raised to be a sissy; you can never transition to being a man. No one would ever buy it. You'd try to pass yourself as a guy, but you end curtsying or running with your hands out or walking with limp wrists and everyone would know immediately what you really were." Bunny's words cut me. He had clearly gone through the same crisis I was experiencing. He knew that it was pointless. I couldn't dwell on what wasn't; I had to live with what was. I never had a chance to be a man, and I never would get one. I would never be anything more than a sissy. I had my father to blame for that, as well as my mother for forcing my father's lifestyle on me just like Bunny and his sissy sisters could only blame their parents for the life they had forced them into. I tried to fall asleep that night, but memories of my childhood kept me up. I was always the junior maid while my sister was the princess. I served her because the gender of her birth entitled her to being revered by someone like me. It was unfair, but there was nothing I could do about it. ----------------------------------------------------------------------- The next morning, I left bright and early with Madame and Miss Denise. Miss Denise drove the car as Madame road in the passenger seat while I sat in dutiful silence in the backseat as we drove to Madame's home. When we got there, Kitty, Missy and Pansy were waiting for me. They helped me carry my belongings to my new quarters. We hung up my uniforms and put away my intimates before Miss Denise ordered Missy and Pansy back to her home. The sissies left Madame's house as Miss Denise, Madame and Kitty looked me over. Miss Denise announced then that I would be marrying Madame the following week. I nodded unable to object it to it, and unsure if I wanted to. Miss Denise then told me that Kitty would be training me to be Madame's sole maid starting the next day. That night, I was left alone with Madame so that we could get acquainted. Madame had me bring her a drink in her parlor. I made the vodka and cranberry drink for her and carried it into the living room for her. She took it from my hand and smiled as I dutifully stood beside her, awaiting her next order. She instructed me to sit. It was a strange order. My mother had never permitted to sit for one second in her parlor. I oddly positioned myself on the edge of her sofa as I looked at her. She took a sip of her drink and noticed my nervousness. She smiled and said, "Relax, Prissy, I'm not going to rip your head off. You have done nothing to displease me so calm down." I smiled and glanced at her, careful not to meet her eyes. Madame smiled at my submissive nature and told me what she wanted for dinner. I knew how to make it, and told her as much. I was then dismissed to make her dinner. It was the first dinner I ever made it by myself, and I presented it to her with a little hesitation. Madame took a bite and said it was acceptable. I thanked her and assured her that I would do my best to improve myself for her. She acknowledged me and said she was certain that I would. After I cleaned up and ate my own dinner, Madame inspected my cleaning of the dishes. Her inspection was very thorough. I found that she was meticulous about cleanliness when it came to all cleaning I did that night. She walked around judged my work and made me re-clean things around her house that she found were not up to her exacting standards. Despite her demanding nature, Madame couched her admonishments with a little praise and the occasional touch of my shoulder or rubbing of my arm. Every time she did that, I would end up walking away from her feeling strange. There was no question that Madame was above me and carried herself as such, but there was something else. She was not as distant with me as my mother and sister were. She was even warmer to me than my father had ever been. I felt a slight amount of joy come over me as I cooked her dinner. I don't know why I felt it, but for the first time in my life I felt as if someone cared about me, even if it was not the best of situations to find myself in. The next morning, I headed to the store with Kitty. I had never ventured out in public for any length of time outside of a vehicle. My father always took care of the shopping, but I was now expected to do Madame's shopping. I knew I would have to learn what it entailed, and Kitty was an experienced teacher. We headed to this market dressed in our uniforms. I felt no different than I normally did as I got out of the car in front of the plain looking building with lighted signs. I smiled as saw all these strange people walking around their cars, going to and from the building, but it quickly left me as I realized they were looking at me to. I saw sneers and heard laughter that I felt was directed at me. Kitty put his arm around my shoulder and said, "You have to get used to it. Most of these people don't like you because of how you look. It's something we all get used to in time." I didn't see how you could get used to glares, sneers and mockery from strangers, but I nodded to Kitty as I walked beside him. We entered the store and Kitty explained how to select certain produce and the importance of buying the exact brand that Madame wanted. I nodded as I walked beside him in the store before we headed for the register. Kitty paid the bill for the food we purchased for Madame and Miss Denise before we headed back to the car. As I tried to understand everything I experienced that first day out in public with Kitty, I was still learning how life would Madame would be. She was very sweet to me, even though she was stern. She expected as much of me as my mother and sister had, but she seemed to have a warmness about her that was absent from them. It was also more than her mother seemed to show her sissy sons. She touched me very tenderly. She would caress my skin as she walked by me. She even hugged me. I was shocked by it. I never knew that a woman would hug a sissy before, but she had no reservations about touching me with affection despite my lowly status. While she let me know I was not her equal or the equal of any woman or man, she let me feel something approaching what my mother gave to my sister. I'm not sure if it was love, but Madame showed some sort of affection for me. However, it always had its bounds. Her affection went no further than a tender touch or kiss on the cheek. Madame explained that she was sharing her life and love with me, but that I was not man enough to share her body with her. That was a right reserved for men, such as Master Thomas. I accepted it. I had too. My lot in life was sealed by my parents. I thought that I could walk out on Madame, but I had only a high school education and no skills other than those of a domestic and no real knowledge of the outside world, so I wasn't sure that I really had the option to leave. The experience of affection, though, kept those thoughts largely at bay. Experiencing affection was not the only thing in my life that was new to me. My body was changing in ways that disturbed me. By our wedding day, I had gained eight pounds. The dress I had been fitted for no longer fit me properly. I saw bulges of flab pushing at the waist of the dress and the rear zipper did not fully close. I felt disgusting in that dress. Madame came into see me shortly before the wedding ceremony. She was dressed in her black form fitting dress that showed off her slender figure that I could have once rivaled if I had had the right curves to accompany my formerly wirily frame. She smiled at me as she said, "Well, it looks like you're porking up nicely?" I blushed at her words as I crossed my arms over my embarrassingly bulging stomach. Her delicate hands touched my bare arms, which made them tingle as she leaned in and kissed my cheek. She smiled and said, "You're going to make such a great wife, my little sow." I blushed again at the praise she mixed in with derision before Miss Denise and my mother came in and took me away for the ceremony. My mother waited with me as Miss Denise took Madame to the altar. I was going to walk down the aisle with my mother, who was the only member of my family to show up. My father was busy training Bunny and my sister would not lower herself to attending the wedding of her lifelong servant. I can't say that I missed having them there. I walked up the aisle past the friends of Madame, Miss Denise and my mother and came to a stop as Madame raised my veil and kissed me before our vows were exchanged. True to her word, she had a new collar for me. She slipped it around my neck shortly after I promised to obey her and be the best sissy she would ever know. The black collar replaced my engagement collar and was locked behind my neck with a gold pad lock. We kissed and received a round of applause from Madame's guests. We went to her home after the wedding as there were several hours between the ceremony and the reception. She smiled at me as she went into her bedroom and slipped out of her dress. I stared at her as she stood before me in her black stockings and garters, bra and heels. She strolled past me and winked as she walked up to the door and opened it. Master Thomas walked in and Frenched her on the spot. He carried her past me and asked me to have a scotch on the rocks ready for him after he finished servicing Madame. I meekly nodded as he took her into the master suite. He closed the door behind him. Still dressed in my wedding dress, I poured him his glass of scotch and tidied up the home a little as I heard Madame's screams of passions. I hung my head for a moment and cursed my father before I grabbed my dust rag and headed into the dining room.

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Be a Sissy

forced to be a Sissy IThe young man stood facing a very large woman sitting in an upholsteredarmchair. There was no other way to describe her. She was fat, perhaps,pushing 300 pounds he thought. The way she was staring at his punyframe suggested that maybe he was going to be her next meal. She wasn'tsaying anything as she visually appraised him for the first time...Jacob had been brought to this woman by his step-grandmother earlierthat morning. He had been given over to his step-grandmother by...

3 years ago
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Sissy On Sissy

SISSY ON SISSY by Throne Bob stood there feeling beyond foolish. His body had been denuded of hair and his skin, after weeks of using an imported emollient, was satiny. All he had on was a pair of bikini-cut panties and a training bra. He was wearing the latter because his wife, Tessa, had taken him to a specialist two weeks before and gotten him a lovely set of breasts. They were small implants and his nipples rode high on their feminine curvature. It didn't provide any modesty...

2 years ago
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Mrs Grant and her new Sissy

New Little Sissy"I'm done planting the flowers Mrs. Grant," I said."Justin honey, I swear I have no idea why you keep coming over to dochores around here.""I am rich you know just like your Mother, I do have a gardener.""There's no need for you to do these things.""Not that I mind paying you, but you certainly can't need the moneyeither.""I just like coming over here Mrs. Grant."She appraised him slowly now, was this a little slip, or was she justimagining things? Was he actually saying he was...

3 years ago
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New Little Sissy

"I'm done planting the flowers Mrs. Grant," I said."Justin honey, I swear I have no idea why you keep coming over to dochores around here.""I am rich you know just like your Mother, I do have a gardener.""There's no need for you to do these things.""Not that I mind paying you, but you certainly can't need the moneyeither.""I just like coming over here Mrs. Grant."She appraised him slowly now, was this a little slip, or was she justimagining things? Was he actually saying he was attracted to...

2 years ago
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Its Hard For This Sissy

IT'S HARD FOR THIS SISSY by Throne Pete had just gotten home from work and he immediately noticed a look of mischief in his wife Andi's pale blue eyes. He seen that all too often in the past. She must have spotted the concern on his face because she wanted to know, "Is something the matter, Petey?" She was calling him by the diminutive of his name. The switch from Pete to Petey was another bad sign. "It's just..." he extemporized, "that you seem... distracted." "Well,...

4 years ago
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stepson becomes moms sissy

Mark Peters let out a low moan that couldn’t be heard above the organ as it played "Here Comes the Bride." Although every other head in the church turned to glimpse the tall, dark-haired beauty imperiously making her way down the aisle, Mark kept his eyes fixed on his feet. Had anyone been paying attention, they would have seen a small tear escape Mark’s eye.It seemed like only yesterday that Mark’s mother and father had split up. Mark’s dad, Mark Senior, was a partner in one of the city’s...

1 year ago
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My Sisters Sissy

My Sister's Sissy By: Missy Satinpanties Note: This isn't one of my usual stories of sexual degradation, but what I think of as "my autobiography that should-have-been." The make- up of my family is the same as it was, my sister's names are the same, but that's about it. This is how I wish things would have gone when my little secret got "out of the bag." I guess I've always been a sissy. I remember playing dress-up with my sister when I was very young, and can vividly remember...

3 years ago
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A Nasty Daddy gets a Naughty Sissy

I came out of the bedroom dressed in my too-short pantyshowing Pink Shorty dress, pretty anklets, black MJ's, pink panties, red lipsticked lips and with my cute cuff and collar set on, awaiting Daddy's padlock, which would begin the playtime for real. This Daddy I had run across on a website was one who loved forcing sissies to literally mess their panties while they were in bondage so he could then go on to the diapering and teasing them for being such bad baby girlie sissies. Me,...

3 years ago
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Sissy Stepson 10 Stepmothers Sissy

Part 10 - Stepmother's Sissy Mrs. Monet put another knee high on the exhausted sissy and got an open toed spike heel with a very small opening in the toe of the shoe. Mrs. Monet forced the shoe on the sissy's limp dick, which started to harden within the shoe. "Come on sissy, just three more milkings, I know your balls ache and your sissy stick is red and sore, but you promised to hump my shoes!" his stepmother cooed. Finally, Caroline's sissy stick got hard enough for the just the tip...

3 years ago
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What does it mean to be a sissy

Sissies are a distinct breed of transvestites. A sissy is a transvestite who’s primary sexual interest lies not just in wearing feminine clothing, but in becoming an exaggerated version of femininity. Femininity as seen through the lens of traditional hetero male sexual desire. Sissies are not seeking to become women in a normal sense, but are instead seeking to become the object of their desires. Their ultimate fantasy woman if they were normal, rather than being a sissy. Sissies are...

1 year ago
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What does it mean to be a sissy

Sissies are a distinct breed of transvestites. A sissy is a transvestite who’s primary sexual interest lies not just in wearing feminine clothing, but in becoming an exaggerated version of femininity. Femininity as seen through the lens of traditional hetero male sexual desire. Sissies are not seeking to become women in a normal sense, but are instead seeking to become the object of their desires. Their ultimate fantasy woman if they were normal, rather than being a sissy. Sissies are...

2 years ago
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What does it mean to be a sissy

Sissies are a distinct breed of transvestites. A sissy is a transvestite who’s primary sexual interest lies not just in wearing feminine clothing, but in becoming an exaggerated version of femininity. Femininity as seen through the lens of traditional hetero male sexual desire. Sissies are not seeking to become women in a normal sense, but are instead seeking to become the object of their desires. Their ultimate fantasy woman if they were normal, rather than being a sissy.Sissies are...

2 years ago
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Ken Sissy

Ken sat there, staring blankly at the movie screen, showing a big black cockplowing into a white beauty. His wife was far from a beauty, as she was now inher early fifties and had put on a few too many pounds for his taste.... butevidently it didn't seem to have bothered the two black men.Ken looked over his shoulder at the entrance to the adult theater, hoping thathis wife would be walking back in, but he knew better. It had all happened sofast, that he tried to remember how he ended up...

3 years ago
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Mistress Sabines Sissy

My phone vibrated softly signaling a text. I almost didn't look at it. I was at a meeting of the board of the corporation I work for, trying to steel my nerves for a presentation I was scheduled to make. This was my first time and instead of running through my presentation in my head I was focused on what I was wearing under my suit.I glanced at the phone."Someone in the room knows exactly what you're wearing..."It was from Mistress Sabine, a woman I'd only met a few weeks ago. She was also the...

1 year ago
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Miss Lindas sissy

My finger was shaking bad as I went to push the doorbell. Miss Linda had told me how my slave training was going to change. She told me she was going to turn me into her sissy slave. Oh My God! What was I doing here? Why did I even come back here? I was afraid of what my heart said in response. The truth was, I really wanted to be a sissy. Even the thought of the intense humiliations that were to follow excited me. I rang the doorbell and felt my doom consume me. Ms. Linda answered the door...

2 years ago
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The Misadventures of the Worlds Worst Sissy

The Misadventures of the World's Worst Sissy By Cassandra Morgan This stuff isn't easy, okay? The world that looks down upon us think that it is. They think that any wimp can be a sissy, that even the frailest of us can scrape and bow and curtsy. They think that anyone can cook or clean are do the so-called mindless tasks that the rest of us are assigned. They think this is a soft life for soft people. They think we are so concerned with being pretty and smelling pretty that...

2 years ago
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First time Sissy

I was born a "boy" but it was mother nature mistake as I am very petite, 5'2" 110LBS. with a sexy round ass and dick sucking lips. For this site purpose I will start at 18 my journey as a sissy cum loving size queen SLUT. In my senior year with a couple of months to go before graduation I turned "legal age" but was no virgin by any stretch of the imagination but cannot talk about it because of "rules". I had become a "male cheerleader" but was finer than some of the bitches there and had the...

Transsexual
2 years ago
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Im Not A Sissy

I'M NOT A SISSY by Throne My name is Joe and not Jodie. I'm an adult and not a kid. And I'm a man and not a simpering sissy. I keep telling myself that. But my wife Arianna thinks differently. I mean, ever since we got married two years ago she had been running my life more and more. Talking down to me. Turning me into her sex slave in the bedroom, demanding oral attentions and giving almost nothing in return. She mocked my small penis and made me masturbate while she watched....

2 years ago
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Richard the Sissy

Richard the Sissy by Joney Cunningham Hi, my name is Richard, or should I say Regina now. I am a sissy. It all started when I was 15 and my parents had taken my 13-year-old sister out of town for the weekend. I had a part-time job, so I couldn't go. My parents told me that the paid Gina, the high school senior across the street to decorate my mom's sewing room. Gina was into interior decorating and had gained a reputation of doing great work. They told me she would have a...

3 years ago
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The Lingerie Salesman Sissy

I had a career change a few years ago. Admittedly a door to door salesman did not sound good but the money was OK as long as I made plenty of commission but the fringe benefits were amazing. For me it was not household cleaners or insurance but sexy lingerie. Not only did the ladies on my round like to try on the lingerie but as soon as they felt super sexy I would get my “extra” commission. Yes I had all shapes, sizes and ages, even a mother and her daughter were regular customers and I had...

4 years ago
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son turned into moms sissy

My name is Barbie. Everyone calls me Barbie because I am small and I have long blond hair. I am the smallest in my class. My real name is Ashley. Before you ask, I do not like Barbie's. I never played with them. I suppose when you have hair down to your shoulders, then people think you look like a girl and call you Barbie. I am eleven years old.I got this diary today. So I might as well write in it. It is a purple one with a bear and heart on the cover. It has a lock on it. I might as well use...

3 years ago
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Cum Craved Sissy

Taking a quick look at the clock, I noticed that the delivery had run late, and I was immediately stressed at the fact that Mistress would be home shortly. I knew I didn't have time to shower, and there was certainly no time for much cleanup either. I just pealed the skin-tight jeans down, crumpled them up and buried them at the bottom of the hamper.I carefully pulled the bright yellow panties down my legs, trying not to make any more mess. I washed the creamy jism away in the sink, squeezed...

2 years ago
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Born a Sissy

Born a Sissy This is the story told by me "grandmother" and my grandson Timmy. Most of it is true and only some parts have been modified. It all started back in 1979 when Timmy was only 9 years old. He was a beautiful child that I loved dearly. Timmy's mother, my daughter, had him at the young age of 17. Being so young she was not quite ready to be a full time mother. She was just like any other teenage girl who had social obligations to meet. She was a good mother but I understood...

2 years ago
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sissy

Thanks Megan for the courage to comment. I like constructive criticism, and in addition, would love to be your toy! This chapter is dedicated to you!After returning to my house, I realized that our shopping trip did not accomplish what we set out to do, which was to get more panties for me to wear. So as not to disappoint Elaine, I dressed, the panties in place of course, and returned to the store. Not sure what to expect I walked slowly through the door.The salesladies smiled and said, "Look...

2 years ago
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From manager to sub sissy

Cindy was a co-worker; well actually I was Her manager. Even though I was Her manger, W/we were very close friends. As a matter of fact I still consider Her my best friend. Everyone in the office was sure that we were having an affair, but we were just friends. I must admit that I would have loved to have an ongoing affair with Her. I know that I am not near man enough for Her and I have always know that from the first time I saw Her. Eventually after being friends for many years, I...

3 years ago
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Irsquom my Wifersquos Sissy

My story starts 2yrs ago when l retired early from work, also at that time l was having trouble with my sex life, so went to see a doctor who informed me l was going through what he described as a male menopause which l never knew existed. My scrotum had shrunk and looked like a shrivelled ping-pong ball, my penis had retreated into my balls and could only be seen if l got an erection which measured almost an inch and with a cock that size l was finding it impossible to please my wife Jolie, so...

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