• Home
  • /
  • Stories Hub
  • /
  • Transgender & Crossdressers
  • /
  • New Beginnings
  • /
  • Page ⁨3⁩

New Beginnings

We all ate and chatted and helped my mom get comfortable. She was glad to be home but was still on the pain killers 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. Sense 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 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 plug in. My outfit seemed to match Diane's secretary suits again. I thought I was going to be weird to return to my apartment dressed in women's business attire and classic style lingerie with high heels, make-up, nails and hair. What would my neighbors say? I went and said good-bye to my mom. She told 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 wish 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 police men 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 I could dart up to my apartment without beings seen in drag. I loaded up Diane's bags to my apartment commenting on heavy they were, and how much things had she 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 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 go to the hotel before I pulled myself from my depression and realized I had once again not brought any clothes. 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 was 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. After which, she sent me off the shower and dress 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 good-bye. I said good-bye 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 for my bad news but tried to cheer me up by saying we could spend some more time together and that things will 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 it was Diane that forced me into lingerie and other pretty things. Along the ride home, we stopped at a couple 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, which 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 gave me a card to a women's clothing store she wanted me to go get all my work clothes from. She said that they will be expecting me the next day and that they will 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 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 maids 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 pad locks 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 everyday by her and my mother, work and live as a woman and be 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 to my face to make me look 100% female even without makeup. The only thing that shows I use to be male is my now small and flaccid penis. The hormones made my skin softer, breast grow to C cups (which I had implants to make them Ds), ass and hips grow proportionately to my breast. My waist was cinched in corsets so long that I have a perfect hour glass 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 positive. I still take care of Diane but we have a real relationship now and have moved passed the bondage, but to it sometimes return 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!

  • Index
  • /
  • Home
  • /
  • Stories Hub
  • /
  • Transgender & Crossdressers
  • /
  • New Beginnings
  • /
  • Page ⁨3⁩

All contents © Copyright 1996-2024. Literotica is a registered trademark.

Desktop versionT.O.S.PrivacyReport a ProblemSupport

Version ⁨1.0.2+1f1b862.6126173⁩

We are testing a new version of this page. It was made in 31 milliseconds