Date: Fri, 22 May 2009 00:17:07 -0700 (PDT)
From: Rebel Doll <rando1000@yahoo.com>
Subject: New Beginings

      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!