Feminized By Mother's assistant - Part 2

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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 comments 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 fits and exposing my feminine undergarments. They went on to make me try on some more panties, camisoles, garter belts, bustiers, stockings, teddies, baby-doll nighty, 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 warned in there and put my panties, camisole, and knee-high stocking in my purse. As we were paying for everything, the saleswoman 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 than and boy in women's clothes. I couldn't argue with her on that. Diane remarked on how the thing 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 stared 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 comments about boy's drool and girls' rules. 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 painkillers 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 fingernails were stripped of their polish, French nail tips attached, and then again painted a deep shiny red. My toenails 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 shoebox 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 hourglass figure, and my fingers nails were long and made my hands look slender and feminine.

Diane escorted me to the Lady's 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 hourglass 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, a red shiny 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 catcalled. 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 into 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's condition (referring to her as her proper name) and even took messages. I would smile when the 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 since 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 a while, 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 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 the 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 a 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.