My Transformation

DianeCuck said:
Thank you for your concern about master being able to take care of us. We have been with him for 20 years now and during that time he has grown his business into 3 gyms, rental commercial properties and rental homes in the Orlando area. Things gyms were closed for a while but they reopened in the summer. Master had a good amount saved and invested in other things so we're not hurting. Some of his tennets are hurting but he's working it out with them.

Considering that you all have been together now for 20 years, if I may ask, did you fully transition?
 
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DianeCuck said:
The next morning I woke up and put on a fresh pair of panties. I assumed since I ate out eve and Darryl said that I wanted to wear panties all the time I might as well do it. I got dressed and then made breakfast for Eve. She didn’t say anything about me eating her out or about the panties, I suppose she figured that the less we talked about it the less awkward it would be. I was still annoyed at Darryl for him ******** me to her like that though and I meant to go over to the gym to talk to him about it.

I went to the gym and met him there. He asked about how was everything at home and that he was sorry that he said what he said but he thought it was for the best for me to not bottle it up and now I can wear panties all I want. I accepted his apology and I told him about the talk that Eve and I had and that I guess I’ll wear panties all the time. He laughed a bit when I told him about me eating her out in my panties and when I told him how wet and horny she was. After that we had our work out. During the work out I noticed he seemed to be much closer to me than usual although it might have just been paranoia and like he always worked out this close to me but I just noticed it.

After the workout we got naked and hoped in the shower. This time though he started to wash me more than usual and I got hard. Before he would just ignore my hard on but this time he took my 4” penis in his large hand which made me feel so small and week and he started to jerk off me off. Between the moans I was letting out I started to protest but he just shushed me and told me to enjoy it. Which I did immensely. The orgasm I had from him jerking me off was the best I have had in my life up to that point. When I did I just melted and he held me and made me felt safe and happy.

As I was drying off Darryl said he had some presents for me. Hearing this made me happy and he said I looked cute when I smiled. I blushed, I should’ve been more embarrassed by this whole thing, especially after he just had his hands on my tiny penis but I was in the afterglow of the orgasm. He gave me the packaged and it was wrapped in pink paper with a black ribbon. I opened it and inside was a matching panty and bra set with stay up stockings. When I saw it Darryl said that if I wanted to I could try them on for him. The way he said it was so sweet and nice and like I didn’t want to insult him by saying no and while I was going out panty shopping those weeks before I thought about other lingerie, what it would be like to wear it. I put on the panties, making sure to tuck my penis just like Darryl had taught me. He helped me with the bra, it was an A cup and I didn’t feel it but it did kind of pushed up the fat I had on my chest. The best was the stay up stockings, the feeling of them rolling up my legs were electric. Once I had them on my legs I was rubbing my legs together and loving the feeling. When I was in the set Darryl asked me to pose for him to show off his presents. I did a few poses not even realizing how much of a girl I was acting at that moment. He complimented me on my weight loss that just made me feel even more of a natural high.

After the posing Darryl told me to put on my clothes over the set and hose. I was worried about the bra showing under my shit but he told me that it didn’t that reassurance was all I needed. He asked me if I wanted more. I nodded. He then said lets go shopping and that he was going to treat me. I was naturally nervous at this. I felt like I couldn’t say no to him since he was being so nice and sweet to me. We went to his car and we drove to a mall. There we went right to Victoria Secret. The image I had in my head of me and Darryl at Victoria Secret looking at panties, bras and stockings was embarrassing. A married white man with a tall in shape black man looking at lingerie. I naturally assumed anyone that saw us knew that these things were for me and I was all red but so turned on by the fact. Darryl bought me about 10 matching sets, 3 of them with garters and stockings. We got back to the gym, which in itself was humiliating because we walked through the gym with Victoria Secrets bags to his office for the other guys at the gym to see.

I gave him a bit of a fashion show and he complimented me on everything I wore. He told me that I could bring the panties home but he wasn’t going to tell Eve about my new gifts and that it would be up to me if I wanted to tell her. I told him it was all too much at once and that I would rather not tell her. I took my presents though and hide them in the trunk of my car, the same place I kept my panties although now I was going to keep those in my dresser since Eve knew about that.

The pattern for that week was I started to wear stockings under my male clothes at work. I didn’t wear the bras just because I was way too paranoid about it showing through my shirts. When I went to the gym now in the shower Darryl was jerking me off and I was loving it.

Friday night while at the gym Darryl told me he was coming over on Saturday for dinner again. Fear swept through me. After what happened at the last dinner I was afraid of what he would say or ****** next. I knew I couldn’t say no, I was getting myself deeper and deeper with him. He came over Saturday night and thankfully nothing happened. It was a normal meal and the only embarrassing thing to happen was he asked Eve if things have improved since I started to wear panties around her and she smiled and conformed that it had. Besides that, everything went normally and I was very thankful for that.

The next day I went to the gym, did our normal workout routine. We were in the shower together, I’ve been loving him jerking me off, even though waves of guilt would wash over me at the same time. One reason was from the situation that I had been digging myself into. The other was the fact that I haven’t jerked off Darryl yet. So Darryl was jerking me off and I touched his cock. It was so hot and wet in the shower and it was just amazing how heavy and big it felt compared to mine. As I touched it began to get better and harder. Darryl said thank you to me. I got his whole 10” fully hard both my hands had to be on it to jerk him. As I was jerking him though he put his hands on my shoulders and gently pushed me down to my knees. I was in a trance focusing on his cock and I let him push me down on my knees. I was there starting right at his cock and looking up at him while he looked down on me with the water going over our bodies. While I was looking up at him and with my hands on his cock he just looks down and tells me that I know to do. I then kissed his cock. I was just a little peck on the head. I looked up and he said again that I knew what to do. I opened my mouth and took him into it. He moans out that I’m a good girl. The first time he refers to me as a girl. Having his cock in my mouth turns me on so much. It is so hot to know that I was making him horny. I move my tongue under the head jerking him off with one hand while my other plays with his balls a bit. It was such a hot erotic moment that I just was living in that moment right then. It didn’t matter that I was married and a father. No I was his girl at that moment and I loved it. I gave him head for about 20 minutes, as he got closer he put his hands behind my head and started to push himself down deeper in my throat, I guess I got about 6” of him inside my mouth before I started to gag and then he would let up and have me be able to breathe more. He started to tense up and told me that I was supposed to keep his cum in my mouth.

He cums and I want to swallow just out of a natural instinct but I don’t, some of it dribbles out of my mouth as he pulls out. He tells me to open my mouth to show him his cum in my mouth. I do and then he tells me to swallow and that I must always swallow his cum. I nodded, the scope of what I had just done washes over me like the water that is still following over our bodies. I’m still on my knees and I asked him are we gay now? He laughed and said no, that he was straight and loved feminity and women. He then said that if he loved girls and I just sucked his cock that I must be a girl then. He then told me to tell him that I was a girl. I repeated that I was a girl humiliating by the whole situation. He said that if I was a girl that I must have a girl’s name. He then told me that he would now call me Diane in private.
this is making my nipples hard.
Victoria(sissy wanna be)
 
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Diane;

can we have some pictures, please?
 
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Yes my feminization continued after I was fired. I got facial feminzation surgery when i was 39 and then implants and orchiectomy (castrated) when i was 40. I live everyday as a woman. When I'm home in usually in lingerie, hose and heels. When I go out 99% of the time I'm in a dress or skirt.

Custer Laststand said:
You're welcome, DianeCuck.

That's amazing. Thanks for reminding us (the forum members) how long it's been since the events occurred that you described in your previous posts. Your and your wife's relationship with your black master and owner has been very stable. I congratulate you for that. Did your feminization continue proceeding well after you were fired from your job about 20 years ago? Did you become fully feminized as a sissy cuckold, such that you are indistinguishable from a woman both at home and when you're out and about? How do you dress, typically, when you're out and about?

Excellent. That's very impressive.

That's good to hear. Your black master and owner has demonstrated excellent foresight and prudence that has enabled him, and thus you and your wife, to survive the present time of economic stress (due to the coronavirus / coven-19, this being late Oct. 2020). And, it's good to hear he's working things out with his tenants who are having financial problems (as opposed to evicting them).

Thank you for filling in the above important aspects of your, your wife's, your wife's children's (sired by your black master), and your black master and owner's lives, including reminding us (i.e., the forum) how long ago the events occurred that you described in your interesting previous posts.
 
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DianeCuck said:
Yes my feminization continued after I was fired. I got facial feminzation surgery when i was 39 and then implants and orchiectomy (castrated) when i was 40. I live everyday as a woman. When I'm home in usually in lingerie, hose and heels. When I go out 99% of the time I'm in a dress or skirt.
Excellent. Congratulations for completing your feminization... i.e., male-to-shemale transition, including castration... Ms. DianeCuck. Today being 1 January 2021: Happy New Year!
 
Wow, hot story! Even my pathetic little dick is stirring in its cage reading this. Now wheres that dildo.................
 
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Very hot story. My ex fucked my boss for 3 years before i found out .I worked out of town lots dah , Sure boss knew she was hot . Why not take care of her for me right
 
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When we get home master throws out any remaining signs of my masculinity. Any male pants or other clothing is thrown out. I also go with him through the house just wearing the lingerie I had on under my clothes at work with his cum inside of me, staining my panties as master also collects all photographs of me as my former male self. He says that I am his girl and that Eve is more his wife than mine and the house needs to reflect that.

Going throughout the house and removing any signs of my former life I was just realizing how far my life has changed with Master now in it. I have become a whole new person at the hands of this man who just fucked me very publically less than an hour ago. Still having his semen inside of me. The former person I pretended to be was no longer alive, I was Diane, sissy slut slave to Master Darryl.

I settled into the domestic life of being maid of two houses. Me without a job meant that bills started to come in and we went through what cash we had saved up paying those bills. I mentioned to Master that I would need to get another job. He told me that he would help me get a job and asked for my resume and sent it out to other accounting firms.

A month goes by and my cash savings has been spent on the bills. Eve has always had her own accounts and relied on me to pay the household bills. Master lays out a business suit outfit for me and he tells me that I have a job interview at a company that was much better than my previous one. I asks him about going as Diane and he tells me that not to worry about it that I am a woman always have to present myself as one.

Master drove me to downtown where the office for this firm was and told me that he would wait for me outside. I asked how I looked and he told me that I was his sexy girl and looked great. Just hearing him give me praise made my clitty jump in my panties.

I walked through the office building of a confidence I never had as a man. I noticed men looking at me in my skirt and blazer. No longer being the overweight loser male I was but now a skinny sexy business woman. I went into the elevator with two other men and they felt like they were closer to me than anyone should be on elevator. One of them complemented my perfume. I said thank you trying my hardest to keep my voice as femme as possible so they wouldn’t know my birth sex.

I got to the office and gave my name as Diane (my male last name), the receptionist looked very confused and said William (male last name). The color from my face disappeared and I just realized that Master sent out my resume with my male name on it. I tried to regain composure and not just crying and run away from there. I just said yes meekly and said down to wait. Tons of thoughts went through my head of trying to think of what I should do and how to explain all of this. Running out of there would have been the best option but I did need the job, I didn’t want to be fully reliant on Master. As I sat there with my thoughts I missed the receptionist calling my name and then she said it louder to break me out of my thoughts. I looked around and other candidates were looking around to see who this William person was who wasn’t paying attention. I stood up the humiliation growing inside.

I walked into a conference room where two older white men were waiting for a William to show up for an interview. When I walked in the receptionist announced me as William (male last name), it felt like a stab into me hearing that name and trying to represent a proper office woman. The two had a confused looked and I just blurted out that William was my male name but I’m a transsexual and go by Diane now. They looked disgusted but went through some simple questions since I guess if they just dismissed me right away they could be facing a lawsuit perhaps. While just sitting there I was on the verge of a breakdown just crying right there, but I was able to hold it together.

After less than 5 minutes they told me that they would let me know their decision, I thanked them for their time and then walked as quickly as I could in my heels out of the office. I started to cry in the elevator and I ran out of the building to Master’s waiting car. He laughed when he asked me how it went. I cried and yelled at him that he put my male name on the resume and it was humiliating to be outted like that. He slapped me across my face and told me to never raise my voice to him. He said he was doing me a favor trying to find me a job and I should be grateful for all the help he has been giving me. He then told me if I was going to cry like a baby I should suck on a pacifier like one but since he didn’t have one he took out his cock and had me suck on his cock while he drove me home.

Master made me sell my car, he said that now I don’t work I don’t have the need for a car and that I couldn’t afford pay for it anyway. I became more reliant on Master. Master would take me to the gym to work out but since my work outs were only for 1-2 hours, I had nothing else to do in the gym after workouts except suck him off or have him fuck me. Gym members would ask him if they could use me and Master added an extra fee to some members for the pleasure of using me. Master set up a closet with a leather couch and I would suck off and get fucked by sweaty gym members. While I was in the room getting fucked by his black gym members having orgasms I never thought I could have my mind went back to the interview and thought that I was much better off doing this than working in an office.
 
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I have always enjoyed following your post - It is good to see that you have come back with another chapter.
 
I know every good story must come to an end. But I wish you would give us some more.
 
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Such hot reading so far!
 
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Diane, you should consider adding your journey to the stories section :)
 
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you are doing great diane. you also have shown your Master your devotion by supporting His choice of having eve be His. keep up the great work.
 
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I am so Happy for you Diane, my wife found out about my sissy side a few years ago now and we act more as sisters than husband and wife.
 
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Every sissy needs to read this!
 
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