Feminized By Mother's assistant - Part 3

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The entire drive home, she would rub my thighs and reach up to my skirt and rub my smooth, satiny crotch. As soon as we got to her townhouse, we began kissing, stripping, rubbing, and slowly making our way to the bed. I made an effort to make sure none of my new clothes were damaged as they were taken off. She stripped me down to my bra, corset and stockings, then laid me down and tied me to her bed. This time she took her panties off, stuck them in my mouth, and duct-taped my mouth shut. She then took a silk scarf and tied it around my head, blindfolding me. I was completely bound to her bed and at her mercy. I could feel her sucking my dick again, but while she did, I could also feel her grease up my ass hole with what felt like lube. This scared me, and I think she could tell as she comforted me and told me that everything was going to be okay and that this time she was going to make me into a real woman. I then felt the extreme pressure of something being forced into my ass. She just kept telling me to relax and let it happen. I tried to relax, but it hurt so bad, and a cried out into my panty gag. After the pressure stopped, I could still feel the object still inside me, then all of a sudden start to vibrate extremely fast. All I could do was moan in pain and in pleasure. Diane told me that every girl's first time hurts but that it gets better. I then felt her mount my dick and ride me even harder than the night before. She would ask me things like, "Are you my little bitch?" and if I didn't reply with or nod yes, I got slapped in the mouth and face. Tears streamed down my face, then she asked me, "Am I your mistress? Do I control your pansy-ass?" then slapped me until I moaned yes. The combination of her slapping me, the dildo in my ass, and her fucking me sent me over the deep end. I came harder than I had ever come before, and it just seemed to keep pumping out of me as she rode me even harder and faster.

As I came and she rode, she started fucking my ass, pumping the dildo in and out of my ass as it vibrated. I finally felt her tense up, grab my throat, and choke as she came all over my crotch. I was so drained that I felt like I could sleep a hundred years. I then felt her get up, remove my gag, mount my face, and told me to suck and lick our girly juices from her. I ate her out, swallowing everything, thinking that I might drown as she rode my face. I pulled on my restraints, moaning, licking, sucking, and cleaned out her vagina like a hummingbird to a flower. I felt her tense up again and cum all over my face, which I also licked up and swallowed. Diane then got up, reapplied my panty gag with fresh duct tape, and I heard her start the shower and close the door to the bathroom, leaving me tied to the bed gagged and covered in our juices. As I laid there while Diane showered, I first thought it bad that I was in that situation, but then thought how amazing the sex was and that I had never had such great sex before. At that moment, I knew that I was officially pussy whipped. I hadn't had sex in a while, and it was nothing like it was with Diane when I did. Despite having to dress in women's clothes and lingerie, I thought I wouldn't mind getting used to it.

I heard the door open, but the shower was still running. Diane then untied me, removed the blindfold, stripped me naked but left the gag to talk to me.

"I'm leaving you gagged so that I can talk uninterrupted. I want you to know that I love your company and spending time with you. I love that you have become so feminine for me, and I will continue to reward you as long as you do and as long as you are here. I meant what I said when I told you that you now belong to me, and I could get used to this with you. We could have so many more adventures, and I have many more things to show you if you commit to me. If you do, then shake your head yes, I will remove your gag but say nothing and simply kiss my pussy, sealing the deal."

I began to think about it as she then began to jack me off. Every man knows that you will do anything as long as a woman does that to you. So, I shook my head yes; she removed the tape and gag, and I bent over and kissed her pussy, tasting her sweet-smelling perfume. She then pulled my face to hers and kissed me deeply on the lips. She finally pulled the dildo out of my ass with a "plop" and sent me to the shower with another strong slap on my ass. I knew that my fate was sealed to hers. After I showered as I had done that morning, I have dressed in silk 1950s style panties, a matching nightgown, and little makeup, after which we fell fast asleep in each other's arms.

The next morning, I was dressed in Diane's secretary-to-work clothes and sent to work with her. With the padded panties, corset, and breast forms plus speaking in a female voice, no one at the office blinked an eye at me being the temporary girl for my mother while she was away. The rest of the week went the same. I was feminized the entire time, worked 8 hours a day as Diane's secretary, went to see my mother in the hospital, then would follow it up with great kinky sex and sleep. I became a pro in heels and lingerie. I also mastered doing regular things with long nails. I would go to lunch with the other secretaries at the firm and obey Diane's orders and wishes. Every now and then, my mom would call and check up on me and ask how I was doing, what I was wearing, and if I enjoyed it. My voyage into womanhood seemed to be forced by Diane and my mother; mostly, it seemed my mother's idea. She didn't know about the sex, but I'm sure my feminization was devised by both women. My mother also encouraged me to call Diane Miss Diane at work as it was more appropriate. She told me again to be on my best behavior and to obey Diane at all costs, and to not get on her bad side as she had a temper. My mom had also stopped calling me by my real name and kept calling me Rachel as everyone else now did. The clothes I had worn there were neglected and got molded and had to be thrown away. I knew I would be driving back home dressed as Rachel.

At the end of the week, my mother was released and sent home. My mom, Diane, and I all went to my mother's house and helped her settle in. Cleaners had come in while she was gone and cleaned up the house, re-carpeted everywhere, and there were no signs of the accident. Diane told me to run my mom a bath, remake her bed, and prepare her some food. As my mom was in the bath, and after I changed the sheets on her bed, Diane told me to hurry up as I was taking too long and the food better be ready when my mom got out of the bath and to serve it to her in bed. I hurried to put the old sheets in the wash and start on the food, but my mom still finished before I could prepare the food. While my mother was dressing and getting into bed, Diane came to me, told me to pull up my skirt and get over her knees. I looked at her in shock, and she just grabbed me by my hair and forced me to do what she said. While I was over her knees, she told me that since I took too long and didn't follow the direction, I would be punished and regret it more next time if I defiled her again. She then wore my ass out with a thin lady's belt. It hurt so badly, and when I went to cry and scream, I felt her panties shoved in my mouth, and I was beaten even harder as I was gagged. After she stopped, I pulled her panties out of my mouth, and handed them back, pulled my skirt down, and collected myself. Diane fixed my makeup and told me she hated to do that but that I must do what she says or I will be punished. She then sent me on my way to finish cooking. I was so dumbstruck at what happed; I had never been spanked like that except when I was a little kid. I knew then never to fuck with Diane and that I was in deeper than I had thought. I thought this was all in fun and some kinky game, but as I massaged my bruised ass, I knew things were now different and wondered if they could go back to normal.

We all ate and chatted and helped my mom get comfortable. She was glad to be home but was still on the painkillers that made her sleep. After getting my mom to bed and I cleaned up the dinner mess, Diane and I went home. At home, we proceeded to a kinky suck and fuck fest with me again as the bitch. Since this was my last night there and I was going home the next day, Diane told me she was sending me back into the world as a real woman. Not knowing what she meant, I soon found out. While I was again gagged, blindfolded, and bound, Diane greased up my ass again, but this time for her huge real feeling strap-on dildo. It looked so real, complete with balls and skin. What happened then can only be described as extremely pornographic. She fucked my ass so hard that I actually came without her ever touching my penis. I then ate her for about an hour and cleaned up after her orgasm. As I thought it was all over, she jerked me off once more into her hand and fed me my own cum, then telling me I was a real woman now. We both showered and got ready for bed, but before I had my panties up, she bent me over the bed and inserted a butt plug in my ass, telling me to leave it in and that it would remind me of her.

In the morning, we had wild sex once more, then showered and dressed, leaving the butt plugin. My outfit seemed to match Diane's secretary suits again. I thought it was going to be weird to return to my apartment dressed in women's business attire and classic style lingerie with high heels, makeup, nails, and hair. What would my neighbors say? I went and said goodbye to my mom. She told me that she now wished I could stay longer so she could see me and help out at her firm as she was told to stay home for a couple more weeks. I told her I wished I could help but had to get back to work myself. After I left, Diane drove me back to the hospital, where I had left my car all week. To my dismay, my car was gone. Security at the hospital said that they didn't have it towed, but it was driven away by someone, whom they thought was the owner. My car was stolen. I then had to go to the police department dressed as a woman but give them all my details, admitting that I was indeed male. I sure got a lot of weird looks after that. Some policemen would walk past me and smile. Diane just told me not to worry and that she would drive me back home.

We went back to her house after filing the report for my stolen car. Diane packed a few bags saying that a girl can never be too careful and to always have variety. I loaded up her car, and she drove me the 4-hour drive back home. Luckily when we got there, it was dark, so that I could dart up to my apartment without beings seen in drag. I loaded up Diane's bags to my apartment, commenting on how heavy they were and how many things she had brought. She only grinned and told me to mind my business. "A girl never asks, and a lady never tells." I began making calls to my work, only to find that I had picked a bad week to take a vacation. It seems that in my absence, a few servers went on the fritz, and no one knew what to do. It got around to the C.E.O. of the company, and he thought he would make an example of me; I was fired for job abandonment. I couldn't believe it; I was now without a job, had rent and bills on the way, and spent what little money I had getting to my mother's side. I fell to the floor and cried. Diane once again comforted me and told me it would all be okay. She said that she would get some movers and put what I wanted to keep in storage and that I could stay with her and help my mom out by being Diane's secretary again. I knew then that I was going to be feminized for a long time. We packed up her car and decided to find a nice hotel to help me cheer up. We went to the hotel before I pulled myself from my depression and realized I had not brought any clothes once again. It seemed that lingerie, dresses, cosmetics, and jewelry would dominate my life as Diane was doing. I slept in a pink baby-doll nightgown with matching panties.

I awoke to Diane making the phone calls to the movers for my things and told me she was taking care of everything. While she was on the phone, she ordered me out of bed, told me to crawl to, and then eat her pussy. As I ate her out, she continued her conversation, telling them to take everything but the furniture into storage, and the rest were theirs. She had made reference to an earlier part of the conversation and said, "no, just throw everything in there away." I later found out that she was talking about my closet full of clothes. She held my head in place to her pussy as she organized the demise of my life in that town. She called and closed all of my utilities, called my work and told them to send my last check to her address, and called and canceled my cell phone as well. I must have eaten her for an hour before she came while she was on the phone with my cell phone provider too. Afterward, she sent me off the shower and dressed in what I found in one particular luggage case. After we were dressed and ate room service, Diane gave me a couple of vitamins and told me that I was going to be healthier and happier in her care. I loaded up her car, and we kissed that place goodbye. I said goodbye to my old life, my friends, my work, any girls I liked, and my independence and freedom, and then I wept.

My mother was sad about my bad news but tried to cheer me up by saying we could spend some more time together and that things would get better for me. She kept calling me Rachel and a girl or young lady. I think that she thinks that I want to be a woman when Diane forced me into lingerie and other pretty things. Along with the ride home, we stopped at a couple of XXX shops, and Diane would buy some things and say that it was to help me cheer up. We passed through another town and stopped for food, only to be hit on by some red necks, one of whom pinched my ass and laughed. We finally made it back and went to my mom's first. She comforted me and also gave me what she called a clothing allowance. She said that if I'm to help at her office, I better look my best and give me a card to a women's clothing store she wanted me to go get all my work clothes from. She said that they would be expecting me the next day and that they would take care of everything. Diane said that she would take me shopping for more lingerie and everyday clothes as well, plus some things she said I would only wear around the house. My mom and Diane went on to plan out my life while in their power. I would live with Diane and be her personal assistant, secretary, and live-in a girlfriend, it seemed. My mother would be taking some much-deserved time off, and Diane would be filling her place, and I would be taking Diane's place.

After leaving my mom's, we went back to Diane's, where I unloaded her car again and put away all of "our" clothes. Diane told me to go into her bathroom and change into the outfit on the back of the door for this evening. On the back of the bathroom door, I found in horror a French maid's outfit, complete with matching lingerie, petticoats, corset, stocking, heels, collar, lace arm gloves, and maids cap. Everything was black and white, satin and lace. After I dressed, Miss Diane inspected my outfit, and I heard a couple of clicks. She had small padlocks and had locked the zipper of the dress to the collar of the dress, a locking collar, locking leather wrest cuffs, the high heels locked, then proceeded to lock me into a chastity belt. I was then gagged with a newly purchased ball gag that also locked. Diane then attached a long chain throughout the collar, cuffs, and ankles on the heels and locked it into place. It made me very restricted to movement and almost hobbling me. I could do simple tasks but would make it very hard to get away. Diane then gave me my orders and welcomed me to my new life; I would be forcibly feminized every day by her and my mother, working and living as a woman and being submissive to all women, mostly her. I now belong to her forever, and I would be her secretary, live-in maid, and personal whore. She told me how she had devised the entire thing as she had wanted me for a long time, but I was always such an asshole to her and other women; now I would know what it felt like.

Epilogue

I now live with Miss Diane full time and have for two years now. I am impotent from the mass amounts of female hormones and have developed a very feminine body. You can consider me a pre-op transsexual. Diane and I have been married as a lesbian couple, and my mother is very happy for us. I also plan to start a line of women's clothes for men (Diane's idea) to show how beautiful women's clothing is and how great it is to be a woman. I have already had some cosmetic surgery on my face to make me look 100% female, even without makeup. The only thing that shows I used to be male is my now small and flaccid penis. The hormones made my skin softer; my breast grew to C cups (which I had implants to make them Ds), ass and hips grew proportionately to my breast. My waist was cinched in corsets so long that I had a perfect hourglass figure. I have quit being a secretary and have moved on to pursue new dreams as a woman.

Along with the clothing line, I have done some modeling for some clothing websites and try to stay busy and cheerful. I still take care of Diane, but we have a real relationship now and have moved past the bondage, but it sometimes returns during sex. I never thought I would be happy as a woman, but I don't know if I was ever happy as a man. Now that I am happy, I'm glad it's in a world of lace, satin, and the other pretty things of womanhood. Hear me roar!