My journey begins as some do, with an accident. My mother had taken a nasty fall at her home. It had flooded due to a busted pipe and slipped while cleaning it up. I was living in another town a few hours away when I got a call about what happened, in which I dropped everything and drove expecting the worse. I was an only child and my father had split when I was very young, so I am very close to my mom. I was getting updates on her condition while I drove the 4 hour trip to my home town by her secretary and close friend, Diane. She informed me that my mom was at the hospital and they were admitting her to stay.
I arrived at the hospital and immediately went to her room. My mom was up and awake with only and busted leg that was wrapped in a cast. After our long hug and greetings, she laughed about the situation and told me it was only a broken leg and thought the whole event was funny. I told her how Diane had made it seem like a life and death ordeal and how it scared me to think the worse; and that I had dropped everything and drove without even packing for a stay.
As we sat and caught up on our lives, Diane walked in told us that it was raining outside and was to be a bad storm. I jumped up and looked out the hospital window to see a near sidewise rain with high winds. My mother saw it as well as I drew the curtains open for all to see. She said that I shouldn't drive back in that kind of weather. As I didn't know the condition of my mother before I arrived, I had phoned my boss and said that needed a week off to assess my mother's condition. My mother thought it was an excessive amount of time to take off work when she only had a broken leg. I had no idea what to expect when I arrived and thought the time off would be sufficient in case the situation was as bad as Diane had made it out to be. We all laughed at each other and the predicament we were now all in. My mother figured that sense I had a week off, I could spend it with her and in my home town. It would be like a small vacation, except I had to visit my mom in the hospital until she could leave.
I now needed a place to stay, and sense my mother's house was flooded and all my old friends had long sense moved away, my mother thought it would be a good idea if a stayed with Diane. She was at least twenty years my senior and a very kept proper woman. She was very classy and very organized and handled most my mother's matters for her. My mom was a very successful business woman and Diane was her right hand lady. Diane did not argue with my mother on her suggestion of me staying with her. My mother added that I had to be on my best behavior and do whatever Diane asked while I was in her home.
After we all said our good-byes, I rode with Diane to her house as it was foolish to drive two cars in bad weather. We stopped for some fast food before we reached her home which was a small but classy townhouse. We ran to the front door and to the covered doorway from the rain. Diane fiddled with her keys in the safety of the covered doorway as I stood behind her getting rained on. It seemed too dark for her to see the keys and I seemed to be getting drenched while she fussed to open the door. After she finally unlocked and opened the door, we rushed inside. Diane saw I was now soaked to the bone and told me to stand there while she got some towels and told me to take off my shoes and strip to my underwear. Hearing my mother's voice in my head, I didn't argue with Diane and embraced her help to get dry and warm. She hurried back with some towels and a terry cloth robe. She wrapped me in the robe and helped dry my long grungy hair. I stood and shivered as she dried me off. She then suggested that I take a hot bath, while she made a fire and prepared some food. I only then took notice to the fact that I had no clothes and brought nothing with me to wear. Diane told me not to worry about it, and that even though she was a few inches taller than me and thicker than my frail form, she should have something for me to wear after I returned from the bath. The clothes I had worn were now soaked and would have to be cleaned at the laundry mat in the morning.
As I entered the very feminine bathroom, Diane gave me a plastic bag to put my remaining soaked underwear in and that I was free to use any of her toiletries. While I bathed she would find me something to wear. I found all kinds of feminine smelling soaps, lotions, shampoos, hair products, make-up, nail polishes and so on. I didn't dare want to use anything I didn't need, and all I needed was to wash my body and hair. I found myself scared to touch anything in that I was in a strange woman's house and I was looking at all her personal hygiene products. Diane ran me a nice bath adding some bubbles and lotions to it saying it would help me relax and warm up. She then helped me put my hair in a shower cap telling me to bath first, remove the water then shower to wash my hair. I felt funny as I stood with all my long hair in a shower cap and wearing a pink terry cloth robe. After she left the bathroom, I stripped, put my wet underwear in the plastic bag, hung up the robe behind the door and stepped into the very hot water. It took me a while to get use to, but when I did, a sat with the water coming up to my collar bone as I soaked. The water was so warm, smelled amazing and had a slight tingle to it.
I must have sat for so long that Diane knocked on the door to check on me. She said I had been in there for almost 45 minutes and my food was getting cold. I must have passed out for a little bit because the bath water was also cold. I then got up, pulled the plunger on the tub to release the water and started the shower head. As I got up a noticed hair floating in the water which I couldn't explain until I began showering and saw all my body hair being washed off. I stood there as I was now as smooth as an Olympic swimmer. I took off the shower cap to wash my hair and then washed my body off with flowery soap. After I cleaned out the tub and turned the water off, I stepped out and found more towels to dry off with. I examined my skin as it was now hairless. I now also smelled like the perfume department at Macy's. I dried off and put on the robe again and brushed out my hair which seemed to be very soft tangle free.
I opened the door and found Diane sitting in the living room next to the fireplace. She asked me how I felt and if I was hungry. I told her I was fine and that I could eat a horse. I then went on to ask about why the bath water made my body hair fall out. She gasped and remarked that she had forgotten that one of the bath lotions was a depilatory hair remover and that she was so sorry. She was so use to making the same bath water for herself that she didn't remember what she even put in it anymore. She told me that my skin looked great and I smelled wonderful. I simply blushed and thanked her for her compliment. She then led me into her bedroom where she said she had found something for me to wear to bed. As she got the clothes, she handed me a bottle of lotion and said that I should put it on all over seeing that the depilatory might burn later and the lotion came with it to soothe the skin after the hair removal. I was so mad that I was now hairless but the burning comment scared me to put the lotion on my legs, arms and torso which felt so good on my now smooth skin. Diane sat some things on her bed and told me to put them on while she re-heated my food and that the terry cloth robe was too wet and laid out another robe.
I examined the clothing she left out for me to wear. On the bed was a burgundy satin and lace robe with matching nightgown and panties. I tried to object on wearing the attire and asked for something else. Diane remarked sternly that she did not make it a hobby to keep men's clothing around and that I was in a woman's house and that she had women's clothes, and if I didn't like I could put on my wet clothes and leave. I could tell she was offended and to quiet the situation, I looked at the ground and remarked that I was sorry to offend her and that I was very thankful for her hospitality and her. As she calmed down, she accepted my apology and warned me to not disobey her in her home again or she would tell my mother, after which she told me to get dressed and be a good "girl" and meet her in the living room to eat. I brushed off the girl comment as a joke and walked to my new attire in horror and shame. I first stripped off my robe and towels and adorned the panties first. I picked them up to feel the fabric and finger the lace edgings which seemed to fascinate me yet immortalize me, it felt like entrapment. I slipped them up my hairless legs and snapped them in place around my waist, hiding my shriveled, pathetic, feminized crotch. The feeling was overwhelming and humiliating at the same time. I felt overpowered and in Diane's control while in her clothes, like she was confining me to satin and lace. I then put on the night gown and shrieked as the cold satin dropped over and caressed my skin, which Diane had to of heard. I then covered myself in the robe to complete the set and outfit and saw on the floor a pair of black low heeled sandals. I figured they were left out for me to wear as well and didn't want to further upset Diane by defiling her again. I felt so ashamed and submissive in my nightwear. The robe had a fur edging around the bottom and around the cuffs. All I wanted to do was go eat, go to sleep and get my clothes cleaned and forget this entire night and go home.
Diane was sitting on the couch watching a movie when I came in. she gasped yet again and put her hands to her mouth and then said that I looked fabulous, a natural beauty. I blushed a deep red at her comment, in which she went on to ask why I had shrieked so loud in her room. I told her about the nightgown and how it was cold along my hairless skin. Diane busted out laughing saying that a screamed like a girl. I now couldn't stop blushing. She pulled me over to the couch and I sat with her as I ate my food and watched her chick flick movie. As we sat, she brushed out me hair and put it into a scrunchy. Diane remarked on the shoes I was wearing and that she didn't leave them out for me but I was welcome to them and that I looked amazing in them. That sent me to a new level of embarrassment, and I continued to stare at the floor and at my feminized feet. Diane reached up and pinched my cheeks saying how rosy they were when I blushed. After her teasing me, I asked where I was sleeping, in which I was shocked to hear I would be sleeping with her. That took me off guard but I thought how nice it would be to sleep in the same bed as a beautiful older woman. She said that she thought it would be kind of nice and warmer for both of us, and that is was just "us girls." I admit I was excited to sleep in bed with an older woman but also very nervous.
Diane went into her room to change and get ready for bed as I cleaned up my mess and put my dishes in the sink. I somehow got sucked into the girly movie she was watching while she was changing. I could smell something weird and looked around for the cause of the smell; I had noticed it when I came out of the bathroom. I found a deep red bottle of nail polish on the coffee table and opened it to see if it was where the smell was coming from. Indeed it was the cause; it had such a strong odor. Just as I was screwing the cap back on, Diane came back and surprised me by saying, "Ah ha, caught you!" She began laughing at how high I jumped and she said that she had just wanted to scare me. She then asked me what I was doing with her nail polish and if I wanted some. I told her that I was just checking on what the smell was in the room and that it was coming from the bottle. She again laughed and told me that while I was the bath, she was touching up her nail polished fingers and toes. She then sat down next to me while taking the bottle from me and told me to give her my hand. Diane said that I would also look good with a little color and that it would match my outfit, this plunged me into shame once again and I didn't even argue with her in fear of making her angry again. We sat and watched the movie as she proceeded to paint all my finger nails and then went on to my toe nails as well. While she feminized my hands and feet, I took notice of what she had changed into. Diane was now wearing an outfit similar to mine except that it was all red satin. Her busty breast had been shaped into cleavage and I could smell the same lotion and perfume on her as I was wearing. She had also put her hair into a high ponytail making her look very strong and superior. After my nails were done, Diane told me stay there and not move, and I had better not mess up my nails. She returned with a small bag and began putting make-up on my face. When I tried to ask what she was doing she said "Shhhhhh" and continued to work on me. I didn't dare stop her as I didn't want to anger her by messing up my nails, make-up and defying her again. Diane put a light foundation, pink eye shadow, eyeliner, mascara, and a pink lip gloss. After she was done, she laid my head in her lap and plucked my eye brows. It hurt so bad, but every time I wanted her to stop she told me to be a big girl and tough it out. She went on to say that men had no idea what women went through to look beautiful and that I was getting a crash course. She thought that I had the body and the face for it and that I should think of the experience as my first girly sleepover. After she finished my eye brows, she powdered the area around them that were red and filled in my brows with a pencil to bring them out more. Diane handed me a small compact with a mirror and I was utterly stunned. I looked like my mom but 20 years younger. Diane said that a lady should always look her best, even for the sand man.
We powered everything off and went to her room to go to sleep. Diane helped me out of my robe and into bed. She did the same by taking off her robe and getting into bed next to me. As we turned to lights off, she told me to cuddle up to her, in which I laid my head on her chest as we held each other. I felt kind of weird but also very comfortable, and with the day I had had I was very sleepy. I felt Diane kiss the top of my head and said "Good night sweaty," and I replied a good night to her as well. As I laid there smelling her sweat aroma, she ran her fingers through my hair, caressed my face and told me how beautiful I looked in her arms. I told Diane that I thought that she was very beautiful too and that she felt good in my arms. Then it really got weird, she kissed me. Not like a light little kiss but with her tongue in my mouth and very forceful. I immediately got turned on as she held me very tightly as we made out. I then felt one of her hands begin to stroke my penis through the satin panties. I have never felt anything that erotic and good before. She then grabbed my hand and made me squeeze her breast. It was so big and felt so good with her satin nightgown. I heard her moan as I squeezed her breast and played with her nipples. I was also moaning as she played with my privates through my satin panties. Diane then pushed me down and got on top while rubbing her pussy on my shaft, dry humping me with our panties still on. I was now playing with both of her breast while she squeezed my nipples through my nightgown. The entire time she was telling me things like "doesn't it feel good to be a girl with a woman," or "I'm going to show you things you've never heard about my little bitch." Normally all these things would have shocked me but I was so turned on I didn't care what she said as long as she didn't stop molesting me. Diane then got up and pulled my panties down and off of me then stuffed them in my mouth. She said that she didn't want to hear me scream at what I was about to do next. She crept down and I watched as she stuck my entire penis in her mouth, and proceeded to blow me like her life depended on it. I tried to scream as it felt incredible through my gag but only muffled cries were heard. It didn't take long before I orgasmed in her mouth and watched her swallow it down. I was still as hard as a rock to which Diane took her panties off and mounted my throbbing member. I was so desensitized now for the blow job that it was now her time to get off. I watched as she bucked and rode me like a carnival ride. She screamed and moaned, and after a while I had feeling again and I joined her in the noise making. We had to have been so loud that the neighbors could hear us. After about an hour fuck fest, we simultaneously had the best orgasm of both our lives and clasped onto each other, panting and moaning. Diane held me in her arms as I shook from such a hard orgasm, covered us up in her blankets and comforted me until we fell asleep, a wet sticky mess.
The next morning I awoke to the shower running and hear Diane moving about in the bathroom. I wiped the sleep from my eyes and noticed the time, we had slept all day and it was now noon. Her bed was so warm and soft that I didn't want to get up. Diane emerged from the bath room with a towel around her body and another wrapped around her head. She told me in such a warm tone to get my lazy pretty ass up and take a shower while the water is still warm. I jumped up and noticed what I was wearing, confirming everything that had happened the night before. My nightgown was sticking to me and my reflection in Diane's vanity mirror showed my make-up smeared all over my face. I was told to shower and give my body a once over with a razor and that I better smell nice when I get out. She said that if I can make myself pretty for her again that there could be a repeat of the prior evening. I totally wanted to have sex with her again and would do anything I could to do it.
I stood in the shower making sure to remove all the make-up and cum from the wild sex, shaved my entire body, washed in her sweat smelling soap and washed my hair with her shampoo and conditioner. When I got out, I towel dried and smeared the perfumed lotion all over my body. I worried that on goers would notice the smell if we went anywhere and began to fear what was happening to me. I walked out of the bathroom in the pink robe again and found some clothes on the bed. Diane appeared from her closet and told me to get dressed in what she said was her most masculine outfit. I dressed in white satin panties with lace edgings, matching camisole, tight black pants, and a white v-neck cashmere sweater. The pants were so tight that my penis seemed to be pushed further between my legs and made my ass stick out. The sweater was so feminine but comfortable. I saw Diane wearing her normal attire; black business suit with skirt, heals, stockings, camisole, blazer, hair in a high ponytail, jewelry, and perfect make-up. I remarked on her beauty with a "wow" in which she replied, "A woman must always look her best ... Rachel." Rachel? Why was she calling me Rachel? My name is Randy. She said that it would be our little secret. She then went to work on my hair, styling, primping and sniped a few "split ends." As she worked on my hair she told me to put on the knee high black stockings and flat Mary Jane shoes. She said the stocking would be more comfortable than socks with those shoes and that that was all she had that would fit me. Everything felt nice but I was worried that I was being dressed too girly and that I just wanted my clothes washed and to go back to normal. I didn't dare tell her that though, she looked so in power and in control and I knew how strong she was by how forceful she was the night before. As if reading my mind, she said that we will have to go wash my clothes later but we had to run some errands and that we had to see my mom in hospital.
As I thought we were done, Diane said how haggard my face looked, that I didn't sleep well and that she might have been a little too rough with me in bed. She went on to recommend a little make-up to hide my crow's feet, flushed skin and tired eyes. I tried to argue on this but she said to trust her and that it would turn her on a little. Excited by her wanting me again, I let her work her magic on my face telling her to be subtle. She sat me at her vanity and began my transformation. I watch as my face was once again feminized to somewhat match hers in a professional female appearance; it was not subtle at all. She gasped at the final product telling me how pretty I was and how wet she was getting. She then had an idea and told me to sit still. She pulled out my little studs from my already pierced ears and put in some pearl studs, followed by a pearl necklace, matching bracelet and a small gold watch. As I tried to protest on the female jewelry, she reached up and rubbed me between my legs telling me how I want to look beautiful for her and my injured mother in the hospital. 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.
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!