My Journey to Sissyhood

I used to think my journey into sissy-hood started innocently enough, but looking back, I realize my Mistress wanted this all along. And when the circumstances were right, she made it happen. It happened so quickly and smoothly I never knew what was happening to me until life as a man for me was over, and I became my Wife's sissy.

My wife and I were the typical couple I suppose, traditional in our home life and usually vanilla in our sex life. I would come home from working all day at the factory and kick back with a cold beer and watch TV while she cooked supper, cleaned the kitchen and did the various other tasks that keep a household going. When her work was done, she would spend the rest of the evening working on her online college courses.

Then one day, my factory closed and I lost my job. I spent the first couple of weeks working on a resume, putting in applications, and calling on my business contacts trying to find a job with no luck. My wife had finished her degree and received a masters in communications. she had a position with a telecommunications company and was spending more and more time at work, and she tried to get me to do some of the housework when I was home since I wasn't working, but I just laughed it off. This went on and a month slipped by, and then another month. It wasn't that I wasn't trying but I had been at the same job since high school, and I wasn't really trained for anything else.

I finally got a call from a company to come for an interview. Great, I thought, I'll get back to work and with us both working we might be able to hire some domestic help. The job wasn't what I was trained for, I mean cable splicing isn't your ordinary run of the mill occupations, but by this time I was going to take just about anything I could get. I got up the morning of my interview, showered, shaved, and went to get dressed. Imagine my surprise when I found there weren't any clean underwear in my dresser. I asked "Honey, where are my clean underwear?" she replied, "If there aren't any in your dresser, then you must be out sweetie." I was pissed. I frantically searched again and found no clean ones anywhere.

I asked her "What the hell am I supposed to do about underwear?" Her reply startled me beyond belief. she said, "Well, you have two options dear. Either go commando, or I'll loan you a pair. I have some that are too big for me, they will probably fit you." I was reluctant to put them on, but I knew I couldn't go to an interview free-balling, so I put on the pair of silky blue panties I had bought for her. My biggest fear was hoping that no one would be able to see an outline of them in my pants, but I soon forgot about what I was wearing, as I had to prepare for my interview. The closer I got, the more nervous I became, and the more I tried to concentrate on the task at hand.

After my interview was done I really had to visit the bathroom before heading back to go home, and went to the restroom to piss. It was then I remembered that I had no fly in my underwear. I went to the restroom feeling very self- conscious, and got back in the car thinking of nothing but the panties covering my butt. When I got home was when things began to get strange. I walked in and noticed the laundry basket with my clothes in it. I automatically walked in to the laundry room and started a load of clothes. I changed out of my suit, and then started supper.

My wife came home to find dinner ready, the table set, and the washer and dryer humming contentedly in the laundry room. She smiled and patted me on the butt, then giggled and asked how the panties felt. I told her I felt strange, almost feminine in them, and couldn't wait to put on some man's underwear again. I washed the dishes, folded my clothes and put them away while she worked in the office on her computer.

The next day, things went back to normal. I spent the day searching for a job and watching sports. When she came home, she had to fix dinner and clean up. "What happened?" she asked " Yesterday you were a great help, and today you haven't done a damn thing." With a gleam in her eyes she said "Maybe I should put you in panties more often." "No way," I told her, "I am still a man, and will not wear panties or do woman's work. I'll be back to work by the end of the week."

The next morning, she asked me how sure I was about getting a job that week. I assured her that I would and was willing to bet on it. Oh, I see she said. What are you willing to bet? I told her to name the stakes. She smiled and told me that if I won the bet I could have anal sex with her, but if I lost she got to pick my clothes and household chores for a week. I agreed, and she said that I had until 5 PM Friday and we shook on those terms.

Friday at 7:00PM, she called and asked about my job status. I had to tell her I had no job. She said that was okay and that she would be late because we needed some things and she was going to stop and get them on her way home. "Don't wait up," she said. "I'll see you in the morning. Be ready to pay the piper honey." And with that she hung up. It was then I remembered our bet. Wondering what was in store for me, I fell asleep in my recliner.

She woke me at 6:00 AM and told me to hit the shower, as we had a busy day in store. I came back to the bedroom to find she had a pink bra and panties laid out. I was told to put them on, and then she handed me a matching pair of pink sweatpants and a tee shirt. I was then put to work cleaning the house. I worked all morning doing chores while she sat and drank coffee. I caught her watching me with an evil grin on her face several times, and asked her what was so funny. Her answer was that she was enjoying a little role reversal, and that she liked being the man while I was the woman. I replied by saying I felt silly working in women's clothing, doing a woman's work.

As the day wore on, she would catch me bent over and pat my ass as she walked by, or give a little whistle and comment on my sexy butt. In spite of myself, I felt my cock grow hard in the panties. "What is happening to me?" I thought. "I shouldn't be getting hard dressed up in pink and doing housework. I felt a change begin to happen, however, the longer I wore the outfit. I found myself beginning to feel that she was in charge, and that I should do whatever it took to please her.

That night, when I began to undress for bed, she told me that I was to keep the underwear and panties on. She then produced a simple cotton gown, and said I was to wear that to bed. I blushed and felt humiliated as I stood before her. She noticed my embarrassment, and assured me that everything would be fine. She hugged me close to her, and we went to sleep. Sunday was more of the same. This time it was purple panties and bra, with lavender pants and tee shirt. As we got into bed Sunday night, she snuggled up to me and told me that she was happy I lost the bet. "You make a good girl," she laughed. "Sleep tight honey; just remember only 5 more days to go."

Monday morning, I rolled out of bed in my gown and padded to the kitchen. I fixed her a cup of coffee and took it to her in bed, waking her gently with a kiss. "MMM, she mumbled, I am really enjoying you treating me this way, but why did you bring me coffee in bed?" "I don't know," I stuttered, "It just felt right. What do you want for breakfast?" I fixed her breakfast and had it waiting for her when she was ready for work. I noticed she was spending a lot of time in our bedroom and called her letting her know what time it was. As she left for work, she told me that my clothes were in the guest bathroom, along with a list of chores for the day. Weird, I thought, but I didn't get a chance to ask any questions as she abruptly left for work.

I cleaned up the kitchen and headed to the bathroom to shower and dress. I found a black maid's uniform with matching stockings, panties and bra waiting for me. A pair of black heels completed the outfit. I also found a note which read "I saved this outfit for you to put on while I was gone to let you have time to get used to it without my being here. You will find that you no longer have access to any of your clothes as the bedroom is locked and I have the keys. I will be home when you least expect me, and you better have your work done like a good girl. Signed, Mistress Angela." "Mistress Angela, what the fuck? I thought. Why did she sign it that way?"

I went to check, and sure enough, there was a lock on our bedroom door. The sweatpants I had worn over the weekend were missing too, so I had no choice. I stood there trembling, and was in a daze as I showered and dressed. I looked at myself in the mirror, and wondered why I was hard under the dress. "This is so wrong, I thought, but it feels strangely right." I set about my chores and didn't notice when Angela came sneaking in. "Hey there sexy, she said. "Come here and let me see you." Red as a beet and a little wobbly on the heels, I went and stood before Her. "How do you feel?" She asked as she rubbed up and down my back. "Like a fool," I replied.

She lifted my skirt and grabbed my cock. "I think you like this. I think you are really one of those sissies I have been checking out on the web. You wouldn't be hard if you weren't a sissy. Are you really a sissy in disguise? Tell me you aren't excited." I couldn't look Her in the eye, and I could not speak a word, but she lifted my chin and looked deep into my eyes. "Let's go do a little more work on you and see just how big a sissy you are."

She led me to the bathroom and told me to strip. When I was naked, she applied depilatory gel to my entire body. I had to sit and wait for 15 minutes while it took effect, and had me to wash it off with scented body wash. Next I was instructed on how fill an enema bag and then hang it as I was told that I would be doing it for myself from now on so I needed to pay attention. Naked and hairless I had to bend over in the shower as Mistress Angela inserted the nozzle in my rectum and then released the flow to fill me up. She told me that I needed to be clean on the inside as well as on the outside. It was only about 30 seconds before the first cramp hit me and since I wasn't expecting this, it was a shock as well as being painful. Mistress heard my groan of pain and patting me on my head told me that I would become used to the feelings, and once I was doing it each day I wouldn't notice the cramps so much in the future. I was made to stand in that position until I was told that I could sit on the toilet and after a few minutes and a couple of more cramps I was allowed to expel the water. After 5 more enema's the water that came out of me was now clear, which indicated that I was clean.

As I stood in the shower watching my body hair fall off I wondered what else would be in store for me. A few finishing touches with a razor, and a little body lotion applied, and I was all set. She applied makeup, false nails, breast forms, and placed a wig on me. I didn't mind everything up until now very much except for the enema, but what happened next made such impression on me I'll never forget. She started in with a pair of tweezers on my eyebrows. I begged and pleaded with her to stop and after about an hour she finally stated that she wasn't done but that she could do more later. I was then told to put my maid's uniform back on. As I looked into the mirror, I saw a woman where a man had been three days before. Once again, my unruly cock grew hard and gave me away. She walked around me several times, laughing and admiring her work.

"You make a better woman than you ever did a man so you are going to be my sissy wife. You are no longer Steve. From now on, you will answer to Stephanie, and you will only address me as Mistress Angela. Furthermore I don't expect any back talk, when I tell you to do something you will need to do what I tell you. Also you must never address me directly until you are recognized and you must only reply to me only in the positive. That means yes Mistress Angela. You must never say no to me, Is that clear?"

"Yes Mistress Angela," I responded as a tear ran down my cheek.

"Don't cry sweetie," she crooned, "You will ruin your makeup. Let's go consummate our new marital arrangement." With that she kissed my cheek and took me by the hand and led me down the hallway toward our bedroom.

She instructed me to wait in the hallway while she got things ready. I stood there not knowing what was in store for me. I have to admit, I was scared and confused as hell, but my cock was as hard as it had ever been. After a few minutes, she finally told me I could come into the room. Hesitatingly I entered the room. The room was dark, with only a few candles burning and she was sitting in a chair wearing what looked like a leather bikini. She told me to come and stand in front of her then ordering, "Take off your dress and drape it over this clothing stand and leave the rest of your clothes on", and I did as instructed. "I want you to kneel down in front of me and kiss my foot and just stay there with your lips on my feet", was her next demand.

Stephanie this is how our marriage will be from now on, your purpose is to only serve me. I've gone through 6 years of going to work and then coming home and work another job taking care of you, well that is all over. I'm going to provide you with everything that you need, and you will take care of me. This is how our love will be from now on, is that clear?"

Kneeling there feeling the top of her left foot, the heat on my lips, and her scent in my nose I replied, "Yes Mistress Angela."

Mistress told me to stand and told me to remove my panties and to hand them to her. She continued to tell me how things were going to be from now on as she stood and had me climb on the bed on my hands and knees. "You will no longer work outside the home, Stephanie. You will handle all the housework and cooking, and I will come home to rest in the evening. From now on you will only wear women's clothes, because that is what you are. You may still have a male sex organ, but you aren't anything close to a male, and you aren't a woman. You are a SISSY! You will wear women's clothes, but you are subservient to males and to women. You exist only to serve Me from this moment forward. I will be in charge of everything, and you will address Me only as Mistress Angela."

Once I was on the bed she began to massage my butt and playing with my cock hanging down. This felt really very good, until I felt something else around my butt. "What the hell is that?" I asked.

"I told you to address me as Mistress Angela! That is my cock, bitch!" She snarled as she climbed between my legs. I felt Her spread something cold and wet on my hole and then I saw only stars as she thrust 14 inches of hard strap-on into my virgin ass. I immediately howled with pain as I felt her forcing the unyielding foreign object into my tight sphincter, "Ooooohhh, No! Please No, take it out, take it out, it hurts so much!"

"Take it!" Mistress yelled, as she unmercifully plowed my virgin sissy pussy. "Oh yeah, I am really going to enjoy having you as My sissy wife." As she continued Her brutal assault on my newly acquired sissy hole continued, it soon stopped hurting and began to feel tolerable. Suddenly and without warning my sphincter muscles relaxed and the assault actually began to be pleasurable. I started bucking my hips and moaning into my pillow. Harder and harder she thrust, until I thought I would split in two. In spite of myself, I knew that soon I would cum. I told Mistress Angela I was going to cum, and she reached around under my bra and twisted my nipples. I shot load after load into the sheets. Less than a minute later, she let out a deep guttural moan and came to Her own powerful climax. she collapsed on top of me and gently stroked my head. She whispered gently in my ear, "Are you ready to assume your duties as my sissy wife now Stephanie?"

"I am ready to be Your wife, Mistress Angela. I will do my best to please You and be a good wife." With that, Mistress Angela stood up allowing me to get up off of the bed. She stood naked with that big black monster still strapped to her hanging down almost to her knees. I was ordered to lick up my cum, and then to lick Her pussy clean. I immediately sucked up my sissy juice and once Her pussy was well-cleaned she stood and ordered me to change the sheets on the bed. I got up and changed the sheets on the bed and just as I was finishing she walked back in totally naked holding a tan stick about two and a half feet long.

She walked over and told me to bend over the foot of the bed and to place my elbows on the bed with my head down. I looked at her and then at the bed and then back to her. "Well! Did you not understand my directive", she inquired? I told you not even an hour ago that you were not to address me unless you have been recognized and that you are never allowed to say no to me. Both of my directives you broke in one sentence not 30 minutes after you lied to me telling me that you wouldn't disobey me. You will now experience the consequence of your disobedience.

I bent over the foot of the bed as instructed and listened to my Mistress Angela on the depths of my transgressions, "You have disobeyed me twice and for each instance you will receive 12 strokes of my cane. You will not move, rub yourself, or try in any other form to impede my progress. If you do we will start all over again. Is that understood?

I told her it was and and that I was ready to accept her punishment. It was a start when I felt the first one and I tried to be as silent as I could but I couldn't hold it back, and she gave me another 5 quick strokes before she told me, "I know that they must hurt, so if you need to cry out or beg me to stop you may, but it will not deter my duty to running this household. We have 18 more before I am done so let's get this over with." She then began again and I howled and begged for her to stop but she didn't and didn't even slow down. She kept up her assault until I finally felt her tapping my shoulder and heard her telling me that we were done. My view of her was altered and I realized that my eyes were full of tears, and I slid off of the edge of the bed not being able to stand. She bent down and held me in her arms pleading with me, "Don't make me have to do anything like that in the future, I know neither one of us enjoys me having to punish you, but you will have to learn to obey me, do you understand?"

"I have another surprise for you dear," Mistress remarked. She stood and walked to her dresser and produced a Flex-o-Belt chastity device from her drawer. She told me to bend back over the foot of the bed telling me I should spread my cheeks. It was the first time that I had touched them and I jumped a little and vocalized the feeling as the pain shot through the muscles in my butt. She commented that she didn't like to cane me like this but it had to be done. I could feel her placing something at the entering of my ass and as she pushed it in about 5 inches I could feel her hold something to my rear area. She told me to stand and then for me to hold a piece of what felt like black plastic or hard leather that was covered in a softer material as she fastened a belt high around my waist. She took the piece I was holding and using her fingers pushed my gonads up inside of the cavity, and then guided my little penis into a place designed to keep it flat and out of the way. Once she was done she inserted that piece into a slot on the piece that went around my waist and was rewarded with a audible, "Click."

I looked down at the device around my waist preventing me from touching myself. I wanted to ask a question but then I didn't want to appear like I was speaking out of turn. She told me to go ahead and get dressed and as I picked up my dress she told me to wait and sit on the foot of the bed. I was still looking at the device when she told me to look up to her and after I did she continued, "I know that you're wondering why I'm making you wear the belt and it is to help you keep your mind on what you are doing. If you are thinking about your own body and sexual release then you won't be thinking about mine. I don't want you to think about yourself because when you do you will be thinking about your relationship with me. You don't have to think about that as I'm thinking about that for you. Now you probably don't understand this right now, but then that is what I'm talking about you don't have to think about those things anymore. What you have to think about are your duties, and those duties at the present is taking care of the house while I'm away. It is also to make sure my girl behaves herself while Mistress is away. Now, go fix me a drink and see to my supper Stephanie."