New Beginnings

byrebeldoll©

I looked down at my completely feminized body and her hand between my legs, and then watched as she pinched my nipples through the sweater and camisole saying that I am hers as longs as I am in her house and that she is so turned on by my beauty. I blushed and put up no fight, only sat there and moaned. She then kissed me on the lips, combining our matching lipstick and told me to just go with it for now and let her have her fun and that I would enjoy the benefits later tonight as she fucked my brains out again. She then sprayed some perfume on my neck, fixed my lipstick, handed me a small clutch bag and told me to get in the car. As we went to leave, we saw that it was still raining and handed me a long fur lined black wool coat and said to button up. With the coat buttoned up it looked like a dress, with the way it went in like a corset on the waist and belled out like a dress on the bottom.

We hurried to the car and proceeded to run all of her errands. She still had to run my mom's business while she was away and did some shopping for herself. We stopped at some women's store at a strip mall and went inside. Diane seemed to know the women that worked there and I heard them talk while I looked at all of the untouchables inside. I heard some comment about me followed by some chatter. Diane bought a few things while she told me to try on some clothes, all things I would never wear. I tried on some more women's pants, sweaters, shirts, blouses, skirts, dresses and a corset. I was mortified at what Diane and the other women had me try on, then making me show them how it fit and exposing my feminine under garments. They went on to make me try on some more panties, camisoles, garter belts, bustiers, stockings, teddies, baby-doll nightys, nightgowns, corsets and even bras. Everything felt alien to me and forbidden. I never thought in a million years I would be trying on lingerie with my mom's friend. The last thing I tried on was a corset with garters, black stockings, black satin and lace thong panties and a bra with small padding in the cups for make-shift breast.

Diane came into the dressing room and rubbed her hands all over my body asking me how I felt, telling me I looked wonderful and to leave on what I was wearing and put back on the trousers, sweater and shoes I was wearing. Diane scooped up what I had warn in there and put my panties, camisole and knee high stocking in my purse. As we were paying for everything, the sales women complimented me on my appearance and hoped that I enjoyed my purchases. As we left with several bags I only then noticed that it looked like a now had breast, in which Diane told me to just go with it and that it would be better to appear a girl rather that and boy in women's clothes. I couldn't argue with her on that. Diane remarked on how the thong didn't show any visible panty line and the corset gave me a better figure and pasture. She then reached out and popped my garters through the pants saying that you could almost see them through the pants and maybe a skirt would have been better with the stockings. I was so embarrassed that I just stared at the ground again.

We went and ate a light lunch and then drove to the hospital to see my mother. I was so scared at what she was going to say about what I was wearing. When we got there, Diane told the nurse at the counter that my mom's secretary and daughter were there to see her, and got the okay to go in. I was so shocked that she referred to me as a girl again. As we walked in, my mother put her hands to her mouth and starred in shock. She screamed and told me how beautiful I looked. Diane went on to tell her about the slumber party and make-over and how my clothes got ruined, so "when in Rome" she said. They sat and laughed, then my mom went on to ask me what all I was wearing. Diane told her, even telling her that I had just got new lingerie from their favorite clothing store. My mom went on to say how jealous she was of me and how pretty I was, and that she never thought that she could have such a gorgeous son, then welcomed me in as her daughter and to women hood. I told her I was only wearing all this for Diane until my clothes were clean. That seemed to disappoint her and Diane to some extent. They both went on to tell me that I should enjoy the experience and that there are so many things to endure and try when it comes to being a girl. They made some stereotypical comment about boys drool and girls rule. It seemed to make my mother happy to see me so feminine and I wanted her to be happy and decided to let it go and take their advice. I mean after all, the clothing was very comfortable (except the corset) and I guess all men do wonder why women wear such things.

We sat and had a nice visit. My mother and Diane kept making comments about what I was wearing and how I looked. My mother would fix my lipstick, say how pretty I also smelled, pointed out the garters through the pants (like Diane had done), recommend some other clothing choices, played with my hair and said that I should also get a manicure. After a couple hours, my mom's pain killers kicked in and we told her we would see her later. As we were leaving, Diane encouraged me to also get a manicure, pedicure and haircut following the "when in Rome" comment again. I went along with her and figured it couldn't get any worse now. We drove down to a boutique/beauty parlor and both got signed up for the works. I was told to go and take off my shoes and stockings and have a seat next to Diane. All of the workers seemed to be of Asian heritage and were very nice, not ever pointing out or noticing that I was a guy. I first had my hair washed, colored, cut and styled. Then my finger nails were stripped of their polish, French nail tips attached and then again painted a deep shiny red. My toe nails were painted a matching color after my feet were primped and polished. I felt like royalty with all these ladies working away on me and plus my expensive lingerie being felt against my skin. They then waxed my eyebrows into even more feminine arches. I was also taken back when they asked if I wanted my bikini line waxed in which I replied no. Diane replied, "The girl is as smooth as a baby down there, her boyfriend loves it."Everyone laughed and I blushed again and even giggled a little. After we were all done, and I waited for my nails to dry, Diane went to the car and got a package from our previous purchases. She came back with a shoe box with some black patent 4 inch open toed high heels in my size and put them on my feet. She told me that a proper lady wears high heels and loves to show off her pretty polished nails. I had to admit I felt and looked beautiful. My hair was now a burgundy color and styled in a 1950 Betty Page look, complete with curls and bangs. I couldn't even recognize myself in the mirror. My body had an hour glass figure and my fingers nails were long and made my hands look slender and feminine.

Diane escorted me to the Ladies room with a bag in her arms, and helped me change into yet another outfit. She locked the door and told me to strip down to my corset. I did as I was commanded, then she pulled out several articles of clothes and helped me into them. First she pulled up a pair of padded panties and a big butt and hips that also seemed to push everything else in such as my cock deep between my legs giving me a very feminine crotch. She then helped me into a fresh pair of beige seamed stockings, being careful to make sure the seams were straight in the back. The next item was a box filled with breast forms and a bottle of glue. Diane smeared the glue on the breast forms then attached them to my chest one at a time, telling me I was going to be a D size breast girl. As I held them in place to dry, it looked like I was feeling myself up with my new huge breasts. I could immediately feel the weight on my chest and in my back. Diane helped me into my first black lace bullet bra to help support my new breast. It took some of the strain away and looked great. Next Diane tightened my corset even more giving my waist even more of an hour glass figure. I was then given a thigh length black lace trimmed silk slip that seemed to give me cleavage and feel amazing on my skin. Then I was put into a black Erica Wool Gabardine skirt, red shinny satin Portrait Collar blouse with the top lace of my slip exposed and the black patent 4 inch open toed heels. All this combined with my pearls, hair, make-up and nails and I was a bombshell. Just before we were done, Diane fixed my make-up and applied a deep red lipstick and more perfume. We kissed each other; she slapped my ass calling me her sexy bitch, grabbed our stuff and headed out. We walked out of the bathroom and all the girls whistled and cat called. It was so fun and exciting to feel so beautiful and glamorous. I felt like I was walking on air (except for the trouble of walking in heels). Diane paid for everything, and we both thanked everyone and left.

As we drove down to my mom's office, I thought how funny it was that twenty four hours ago I was a skinny long haired punk, and now I was a beautiful classy looking woman all thanks to Diane. She rubbed my stocking covered thighs as she drove, kept telling me how hot I was and she couldn't wait to get me home. I just sat there and blushed. I did thank her for everything and told her how great I felt and that I was very thankful for her hospitality and guidance. She told me that I made a very beautiful woman and that I was her girl and wished that that week would never end. I was so happy at that moment.

At my mom's office, we went in and Diane told me to sit at her desk while she went in to my mom's office to handle a few things and told me to answer the phone if it rang. I had seen Diane at work before and spoke to her on the phone many times that I knew the greeting by heart to say if someone called. Before she left she whispered in my ear to talk in a female voice as I didn't want to attract attention as a transvestite. That worried me and I worked on a very convincing voice as I waited. Sitting at a secretary's desk dressed as I was made me feel even more in the world of women.

Some people would walk by and smile and I would smile back. I ended up answering the phone a few times, telling them of my mother condition (referring to her as her proper name) and even took messages. I would smile when then person on the other end would call me "ma'am" or "miss," it confirmed that my girly voice was working and I was passing as a girl over the phone; I bet I could pass for real. Then the thought hit me, why would I want to pass as a woman? Did I secretly enjoy my forced transformation into womanhood? Did I now want to be a woman? Of course not, I just having fun, I shouldn't let this stuff get to my head. Just go along with the ride until I could get back to my bachelor pad, I.T. job and men's clothes and habits.

Diane came out and said that sense I had experience with computers, if I would type up a few things for her to help her catch up on her work. It was only a few letters and e-mails. After awhile, Diane kept bringing me more work to do, filing, get her coffee, more typing, answering calls, making copies and delivering things to other people within the firm. I was now Diane's secretary. It was a complete role reversal, I was a now a submissive female worker and she was the powerful boss, even if only temporary. I then answered the phone to hear my mom on the other end. I said, "Thank you for calling Mrs. Swanson's desk, this is Rachel, how may I help you?" She replied back with, "Well Rachel, are you being a good girl and helping Diane catch up on her work?" I told her I was and that I was happy to help them out seeing that she was out of work because of her leg. She told me that even though she was in the hospital that she had a business to run and that it couldn't fall apart because she got hurt. I told her I didn't mind helping until she got better and that I did have the week off. That was my biggest mistake I could have made. I had just signed my life away and didn't even know it.

After finishing many hours later, Diane took me out to eat at a nice restaurant complete with lots of white wine and sexually suggestive conversation. She kept telling me how good I looked and what she was going to do to me in bed to show her appreciation for helping her at work. After we left and were in the car, she could not keep her hands off of me. The entire drive home, she would rub my thighs and reach up 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 the 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 force 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 the sudden start to vibrate extremely fast. All I could is 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 ever 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 humming bird 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 awhile and when I did it was nothing like it was with Diane. Despite having to dress in women's clothes and lingerie, I thought I wouldn't mind getting use to it.

I heard the door open but the shower 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 use 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 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 sweat smelling perfume. She then pulled my face to hers and kissed my 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 was dressed in silk 1950s style panties, matching nightgown and little make-up, after which we fell fast asleep in each other's arms.

The next morning, I was dressed in Diane's secretary 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 I 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 cost, 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 sense I took too long and didn't follow direction that I would be punished and that I would 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 make-up 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 a massaged my bruised ass I knew things were now different and wondered if they could go back to normal.

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byrebeldoll© 18 comments/ 200756 views/ 84 favorites

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