Ever since I can remember, I always knew I was a sissy. Whether as a grade school kid, jealous of the girls who got to wear pretty, pink, flowery dresses to school or as a young adolescent sneaking into my parents’ room to try on my mother’s not-so-stylish panties, I always had a strong desire to be feminine. And also in gym class when I saw the other masculine, muscular boys and deep down I knew that I was not a man like them. I could never compare to their manliness, nor their raw, physical power. I always had a mild nature, fittingly feminine, and in stark contrast to the aggressive, testosterone-inspired young men all around me.

When I started to date girls, I always was jealous of their beautiful, soft skin, and their feminine figures, wishing that I could have the same form. On the occasion that one of them left and article of clothing behind, I always tried it on and entered a state of ecstasy just with the feeling of it upon my skin. When we had sex, I was jealous that their bodies were opening up to receive my cock. And likewise, when they performed oral sex, I was always jealous that they got to swallow that delicious-tasting cum (I had tested my own and from that point forward, always cleaned mine up when I masturbated). But I also could tell very clearly that my small, feminine penis could not satisfy any of the girls I dated. Nevertheless, I kept trying, ignoring my sissiness that must have been so apparent to all of them.

Eventually, I fell in love with a beautiful, strong, dominant woman and we got married. We enjoyed a wonderful relationship for nearly six years before we decided to try to begin having children. Despite having sex regularly, she never got pregnant. It became increasingly obvious that my lack of virility was the problem. My sissy, feminine sperm could do nothing to fertilize an egg. I realized that no matter how much I lived in denial of being a sissy, my body told the truth.

After a year of trying to have children, I finally made the very bold move of informing my wife that I had been cross-dressing since I was 14 and knew in my heart that I was a sissy. She was very accepting and, in fact, encouraged me to further feminize and sissify myself. We perused various lingerie and women’s clothing catalogues and looked online for clothes that would fit me and help me express my feminine self. We even allotted a decent portion of our monthly budget to purchase me sissy clothes so that I could build a wardrobe of feminine attire.

As time went on, my wife seemed to be enjoying her role as the dominant more and more. She told me since I was a sissy, she expected me to perform all of the sissy tasks at home, including cooking, washing dishes, sweeping, mopping, vacuuming, doing the laundry, cleaning the bathroom, ironing her clothes before she left for work in the morning, and so forth. I took to these tasks with great enthusiasm, happy to finally live the sissy life I had always desired. To perform the tasks, she bought me a French maid uniform that she demanded that I always wear when I was working as her maid, and she also purchased a frilly, flowery apron, and flower-adorned rubber gloves that I was to use whenever I did the housework.

My wife, or “Mistress” as I now called her, became increasingly demanding. She inspected each of my tasks and punished me with spanking whenever I failed to perform perfectly, even if I only overlooked a minor detail. I looked forward to her punishment as a good way for her to help feminize and sissify me and to bend me to her will. Soon I became her slave-maid, never questioning her commands, and obeying her even to the most minute detail. She was now my owner, and I, her property.

As my Mistress feminized me, she found it necessary to seek professional help. She enrolled me in a week-long cosmetics course at the local technical college, where I learned how to apply my make-up, how to dress more fashionably, and how to do my hair as to appear feminine and slutty. She purchases three wigs for me to wear and insisted that I don them at all times. She also insisted that I begin taking the “pink patch” diet regimen to help me slim down. She now required that I wear make-up at all times and punished me with facial slaps if I ever appeared in her presence without my appropriate make-up, wig, and so forth. I began setting my alarm each morning an hour before hers (so, at 5:30 am) so that I would have ample time to wake up, shower, put on my make-up, and get dressed in my sissy clothes, before she awoke to the breakfast I had prepared for her.

After just eight months of my Mistress’s program of feminizing and sissifying me, it occurred to me that we had hardly had sex since I had come out of the closet as a sissy. In fact, I couldn’t remember the last time we had been naked together like that. So I broached the subject with her and she told me that I could no longer satisfy her. She told me to seek professional help in sissifying myself by looking online, where I discovered the talented, beautiful, and wise Mistress Amanda. In my very first phone session with Mistress Amanda, she explained to me that I was the perfect type of person to be a sissy cuckold, that is, the perfect submissive, feminized sissy whose wife should have boyfriends and be able to have sex with other men, sometimes at my own audience. It had never occurred to me, but Mistress Amanda’s suggestion tantalized me, especially when she said, “Seeing as you cannot satisfy your wife and that you are a sissy, she probably already has a boyfriend who is satisfying her needs.”

That evening, I broached the subject with my wife and she told me that I could never satisfy her again. She explained that I was a sissy and that I was unsuitable to ever have sex with her again, though she would let me pleasure her with my tongue. I told her that I hoped she would find a boyfriend soon who could please her because I longed to be her sissy cuckold husband. She nodded and said that she would now have the right to go out whenever she pleased, stay out as late as she pleased, and that I should not ask her anything about it. I agreed with a curtsey (as had become our custom by now). She also said, that for my sake, and as a further act of sissification, that she would now conduct dildo training with me so she could transform my ass into a good, workable, useable pussy. We began that training and I grew to crave the slight soreness that resulted from her spreading open my cheeks and emasculating me from behind.

After waiting a month and a half, I grew impatient. After another phone session with Mistress Amanda, I finally asked my wife if she had found a boyfriend. She informed me that she indeed had been seeing a man with whom she worked, and that they had been having sex regularly throughout that period. I was overjoyed. Her pleasure was everything to me, and given that I was a sissy and unworthy and incapable of pleasing her, I felt that it was so appropriate that another man should be fucking my wife on a regular basis. I had no idea what I was getting into.

The next day, she called me from work (I work at home) and told me that she was bringing her boyfriend home after work. She told me to cook dinner for them and that I was to serve them as their serving wench while he was there for the evening. I was overcome with ecstasy so much that I was visibly shaking. I had no idea what to expect, but knew that I must be on my best behavior! I put on my black bra with my French maid uniform, then put on some pink panties with a matching pink garter, and then slid on some black thigh-high stockings, and finally a pair of black leather 4-inch heeled boots, all taken from the sissy wardrobe that my Mistress and I had built up over the previous months. I made sure to put on my make-up, going heavy on the mascara to appear slutty, and also put on several extra splashes of my most seductive perfume so that I would be as sexy as possible.

After many moments of tense waiting, they arrived. My wife seemed excited for me to meet her boyfriend, as if she was flaunting him in front of me. And I quickly understood why. He was so masculine in comparison to me, with defined arm and shoulder muscles that bulged from underneath his shirt. He extended a hand and introduced himself. I simply curtsied and said, “I am my Mistress’s obedient, submissive sissy bitch and you may refer to me as such, if you like.” He nodded with a smile as I took their coats and hung them up. They told me they each wanted a glass of wine, so I went into the kitchen and fetched it for them as they moved to cuddle on the couch. I could tell immediately that they were really into each other, and that made me so happy inside. I had cooked spaghetti that I then brought out on plates and served it to them. Then I got down on my knees and massaged my wife’s feet and then her boyfriend’s, as they enjoyed their meals. They critiqued the food and told me how to improve it next time and I made mental notes of all of their requirements.

Once they had finished eating, they told me that we needed to talk about their expectations of me as a sissy cuckold. First, my wife told me that she had been having an affair over nine months. I was overjoyed to hear that she had been cheating on me for so long and with such a masculine man. It made me feel like such a good, obedient, submissive sissy cuckold to know that another man had been fucking my wife for nearly nine months behind my back! It was becoming increasingly clear to me that my wife wasn’t just flaunting her boyfriend in front of me, but they were actually fairly serious.

My wife looked at her boyfriend, as if to say, “tell her.” He looked at me and said, “your wife and I have decided that you will serve me as my sissy bitch, cock-sucking cum drinker, and pussy slave. We intend to transform you from your current state into a cock-craving, obedient, sissy cuckold. You may still please her with your tongue, but your main duties now will be to serve me, your wife’s boyfriend, as my bitch. I will train you to suck my cock and expect you to give me blowjobs on a regular basis. Once you have proven yourself a good cocksucker, we will move on to transforming your ass into a good, obedient, sissy pussy that will be broken down and made to receive my cock whenever I feel like fucking you. Are you ready to be my sissy bitch, Julie Ann?”

I was clearly blushing now and even sweating a little as my heart beat a million times a minute. I had never wanted anything so bad in all my life. “Yes, Master. I am ready to be your obedient sissy cuckold. I will serve you and Mistress subserviently and submissively.” He replied, “Good.” Then my wife cut in, “Tomorrow we are going to get rid of most of your boy clothes. You won’t be needing them since you will now dress 24/7 as a sissy. We will give you an allowance taken from part of your monthly paycheck (I work from home) and the rest will be split between your Master and Me. Your allowance should go towards buying sissy clothes, make-up, and taking feminization, sissification, and emasculation courses, like the sort of thing Mistress Amanda does. You have only begun your journey and we expect you to continue to please us and customize yourself to our likes. Are you ready for this, sissy girl?”

“Yes, Mistress,” I replied. “I am ready to become a complete sissy. Thank you both for taking control of me and force sissifying me. I am so grateful and I hope to serve you both perfectly in the days and months to come.”

They then informed me of the rigors of my training. They said that I should expect to be spanked regularly, especially in the beginning, since I would be making so many mistakes and that it would be necessary to correct my behavior. My Mistress had spanked me before, so I understood the importance of this, but really looked forward to being spanked by my Master, too. They also said that my Master would have the right to slap me around a little, too, for my serious oversights on my part. I readily agreed with another curtsey.

Jan.25,2010