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.