Date: Wed, 20 Jun 2001 20:57:13 EDT
From: NCDaveBowl@aol.com
Subject: A New Life for Diane

I met Rob shortly after starting work for a new company. He is a senior
manager from a different department. At the time I knew he was a manger but
hadn't met him until that fateful day. I myself have been a closet
crossdresser for years but had not been active recently. I'm not sure what
he saw in me because no one had ever suspected this tendency in me (as far
as I know at least). But while I was in the restroom Rob came in and took
the empty urinal next to me. He spoke up first, asking if I was new. I told
him that yes and informed him which department I worked for. As we were
washing up he spoke up again, asking me how long I had been
crossdressing. Well I was shocked and I suppose my face gave me away. I
puttered and tried to get denials out but he held up a hand to silence
me. "Don't worry, you're secret is safe with me". I remained quiet for a
moment before asking him how he knew. He replied that it wasn't anything
that gave me away, just a feeling he had. He told me that he had always
been an admirer and was currently between lovers. He asked if I was doing
anything for lunch. When I replied that I wasn't, he suggested we get
something together. Since he lived close to work, he suggested we stop and
get some sandwiches and go to his house. For some reason I agreed and off
we went.

Now I must give some background details. I am neither beautiful or
handsome, just a middle of the road type of person. I am tall, and at 6'
usually tower when in heels. I keep myself trim, 165-170lbs and have kept
my light brown hair shoulder length ever since I was a teenager (I am now
40 years old). Ron on the other hand is 6'6", about 250lbs with thinning
brown hair and gorgeous blue eyes. I wasn't sure at the time but later
found out that he is 48 years old.

We picked up a couple of burgers and arrived at his home a few minutes
later. I was surprised to find myself at a very large brick home in the
English Tudor style. It was fairly private, away from the road with lots of
trees and bushes on a large lot. Running along the back of the home I could
see a golf course through the trees. He smiled a bit and told me to hurry
up. We went into a huge foyer, past a living room and into a beautiful
kitchen with a table towards the back which looked out the rear of the
house with a view of the back yard and pool. I was flabbergasted as I sat
down to begin eating. Ron began asking me questions as we ate. I told him
about myself, how I began dressing and how often I had managed to dress
over the years. He nodded and kept prompting me for more information. It
turns out he was very good at putting me at ease. Before I knew it I had
told him most of my story and was laughing and joking around. It didn't
seem like we had been gone long when I looked down at my watch and saw we
had been away from the office for over an hour already. I was shocked and
told Rob I had better get back. He told me not to worry, that he knew my
boss and was going to call in and tell them I wouldn't be back.  I was a
bit worried, not about Rob but about work, and told this to him. He told me
not to worry that they wouldn't fire me, and if they did, he would hire me
up right away. I relaxed a bit as he called my manager.  I don't know what
he told him but he was relaxed and in a great mood as he came back to the
table. He told me about himself. He had tried marriage but found it wasn't
for him. Not the marriage part, but the woman part. He said he considers
himself sort of bisexual. He only has relationships with transgender men
like myself now. I told Rob that I had had a few encounters over the years
but nothing you would consider a relationship. In every one of them I was
always dressed and they were all with men. I told Rob that I suppose that
meant I was gay, but that it just felt natural to me and I always felt like
the woman. He smiled at this and told me that he had noticed me since I
began working a couple of weeks earlier. He had been alone for almost 3
years now and when he saw me he was thunderstruck and just knew that I was
the one for him. I blushed while he was telling me all this, but was
pleased. I admitted to him that he was very attractive as well. He asked me
how many outfits I had currently.  I frowned and confessed that I had
virtually none. Since I had recently moved, I had cleaned out my
wardrobe. Most of my items were very old and worn. I only had a few pieces
of lingerie and 3 pairs of heels. Rob was unfazed by this and suggested we
go shopping. He said he knew all the shops in the area that would let me
try things on and would assist in my selections. I was naturally nervous
since I had made most of my purchases through the mail. But his exuberance
picked me up and got me going. As we went out to the car, Rob came over to
my side of the car and opened my door for me. I was momentarily confused
since no one had done that for me before. As I got in Rob laughed and said
I needed to practice getting in and out of the car like a lady, and to get
used to it. He always opened the door for his lady. My mind was swirling
around as I waited for him to walk around the car and get in. His lady? It
was thrilling, no one had ever referred to me as that before, and I loved
it.

As he pulled away he looked over and asked, where first? Your hair is long
enough so you don't need a wig. Wait I know! There's a special lingerie
shop that we should go to first. And off we went. We went out the highway
towards the airport and arrived at Stacey's Lingerie Shop. As we entered I
noticed that this was no sleazy shop but very upscale with lots of nice
items I would love but would break my bank account if I purchased very
much. There was no one in the store except for an older woman coming
towards us down the main aisle. "Rob" she exclaimed, "I haven't seen you in
ages, and who is this with you?" Rob looked over at me with a questioning
look. I was a bit nervous and shy but replied "Diane" softly. "Stacey, I
would like to present Diane to you. We are in your hands this
afternoon. But, I don't want to spend the entire time here. I'm sure we'll
be back at a later time" Rob stated with a smile. Stacey smiled and asked
us what we had in mind.  Rob said he wanted to start out with a pair of
breast-forms and then get the basic lingerie and nightwear. Stacey smiled
as she grabbed my arm, exclaiming how much fun I was going to have. She
took me into a dressing area and told me to remove my clothes down to my
underwear, which happened to be a white pair of women's panties. She smiled
approvingly as we saw this, and commented on my hairless body. I told her
that I had kept myself smooth since high school as she proceeded to take
all kinds of measurements. Stacey disappeared into the back for a moment
and returned with a small box. She set it on a table and washed off my
chest with some rubbing alcohol. "It's nice that you keep yourself so
smooth, it's going to make this so easy" Stacey stated. I thanked her and
said that my body hair grew so slowly it wasn't a big problem. She then
took two breast forms out of the box and held one up to my chest. I was
amazed. I had heard about them but never seen one up close like this and
never against my body. I hesitantly asked her what they cost. Stacey
laughed. "Girl, you don't think you're going to have to pay for these do
you? I know Rob well enough to know that he'll buy you anything! I can see
it in his eyes. He's never had it this bad before, I think you're the last
girl for him. Unless you don't like him of course." "Oh, it's not that" I
replied. "I really like him a lot, but we just met and this is happening so
fast for me". Stacey just told me to relax and enjoy it. It looks like
you're going to have a fun Friday evening and weekend ahead of you. Stacey
proceeded to apply adhesive to the forms and situate them on my chest,
explaining how to do it and the maintenance I would have to perform to keep
them in tip-top condition. When they were in place I was amazed. They
pulled on my chest and felt so wonderful. I admired myself in a mirror
while Stacey again disappeared in the back. She came back with an arm full
of clothes and a makeup kit. She set things down and showed me how to blend
the edges of the breast forms with my body so the edges were virtually
invisible without close inspection. She then let me apply some light makeup
with suggestions on what colors looked best on me. "We can't let you shop
like that, so try these on for now" Stacey told me. I pulled on a teal
sundress and tan low-heeled sandals. Stacey approved, "Now you look like
any of my customers, so let's go see what you want to buy". Stacey led me
out into the store. Rob was waiting and just stared at me with his mouth
wide open. "Damn, you look great Diane" he told me. I thanked him as Stacey
pulled me along to the bra section. She handed me a basket while she talked
with Rob regarding what he had in mind. They picked out several bras,
standard, demi-cup, strapless, etc along with a few colored bras with
matching panties. Stacey then smiled "I know you love nylons Rob, so lets
get a few garters and nylons for Diane". I was in heaven. I loved the feel
of nylons and now I could just pick them out. We picked up several pair
along with 5 different garter sets. Next came the eveningwear. Rob knew
exactly what he liked and I concurred with everything. We eventually
settled on 3 teddies with attached garters, 6 bustiers (3 of them with
garters attached), and 3 nightgowns (2 short ones and 1 full length). I was
a bit nervous as we approached the counter. I had never thought about
purchasing this many items before and although I was sure Rob was going to
pay, I wasn't sure how all this fit together. As Stacey rang up the items
she told me to keep the items I was wearing and that I could return them
later. I blushed and smiled at the thought of going back outside exactly as
I was now.  Rob pulled out a credit card and didn't bat an eye as the total
was rung up. We gathered up my bags and said our good-byes to Stacey as we
headed for the door. We placed the bags in Rob's trunk and he opened the
door for me. I sat down and swung my legs in., This was the first time I
had done this as a passenger and it felt so wonderful. I felt like a
princess.

As Rob got in the car I nervously broached the subject of repaying him for
the clothing. He laughed and told me he was hurt. He faced me and told me
not to worry because he wanted to do this and not to feel intimidated but
that he had already fallen for me. I wasn't totally surprised but was still
a bit shocked. I wasn't nervous or scared but just that uncertain feeling
when things happen so quickly. I guess it was because I was already forming
feelings for Rob as well. Well we were off to a boutique that Rob said he
had visited before but was not transgender friendly. Since I was en femme,
and very passable, he figured we could get by with it. With him beside me I
was getting more and more confident as we entered the shop. We shopped for
quite a while in the boutique. We settled on 4 skirts, 8 blouses, 3 short
dresses, 1 long dress, and 2 evening gowns, which I thought were overkill
but Rob insisted. I asked him where I would ever wear them? He just smiled
and said he always had to attend social functions and he hated to go
alone. I blushed at the thought and my nervousness arose as we checked
out. But I realized as we headed out of the store that I shouldn't feel
nervous at all. This was what I had always wanted, and the perfect
situation to try it out so to speak.

Rob said the next stop was the mall. He said we needed to get me some
shoes, jewelry, and my ears pierced. I told him I hoped this would be it as
I was getting a bit worn out. We went into the mall and he talked me into
getting a total of 10 pairs of shoes with varying heel size and in various
colors to match the clothes we purchased. I must admit it was so much more
fun getting them in a store versus mail order. As we left I told Rob I had
no problem with my ears as long as it was just 1 piercing and he didn't
spend too much on jewelry. He agreed and I proceeded to have my ears
pierced. I was really excited as the posts were put in my ears. I listened
as the attendant informed me on the instructions of cleaning my ears and
turning the posts until they were healed, at which point I could wear any
other earrings. We proceeded to buy several other pair of earrings and a
couple of inexpensive necklaces.

We then went next door to a salon where Rob told them how he wanted my hair
and told me he would be right back. I sat in the chair and completely
turned myself over to them without really thinking of the ramifications. I
was enjoying myself so much that I was not clearly thinking about how I
would ever return to work with my hair done up and with feminine earrings
in both ears.  They shaped my bangs, layered the back and sides and before
I knew it they were done. God! I had never been able to get my hair to look
anything like that! I must admit that I was even more passable once my hair
was done. Rob was smiling as I met him out front and after he paid we
headed back to the car. I hadn't even thought of where he had disappeared
to until he sat me down on a bench outside in the parking lot. He pulled a
box out of his pocket, opened it and asked if I would marry him. I was
flabbergasted! Here I was, dressed as a woman fully for less than 12 hours
and with a man already proposing. He went on to tell me not to be
overwhelmed but that he wanted everyone to know I was his.  We couldn't
actually get married right now but that I could be his fiancé. I just
kept staring at the ring and at him, moving my eyes back and forth. I must
admit it was a beautiful ring. It was a solitaire diamond that looked
huge. I turned out to be only 1/2 a Carat but it was beautiful. I looked
into his eyes and could see the love he had for me. I told him yes, that I
would be honored to wear his ring and be his fiancé but told him we
needed to slow down or else I was going to faint!  Rob laughed as he pulled
the ring out and put it on my finger. I looked down and realized that I was
home. This was who I was meant to be and whom I was meant to be with.

As we drove back to Rob's house everything started to hit me. It's not that
I panicked but I was unsure where things were headed and what Rob
expected. As we pulled in I knew we had to get things settled so I knew
where everything stood. Rob opened my door and we gathered as many bags as
possible and headed inside. We deposited them in the family room and he
headed back out to get the rest. I sat down on the couch and waited for him
to return. As Rob deposited the last of the bags I told him we needed to
talk. That got a worried look on his face but I continued. "Rob, I need to
know where I stand and where and how this is continuing. I didn't really
think earlier and with my hair and ears like this it's going to be really
tough going to work and back to my apartment." Rob laughed a bit and told
me that it was all up to me, but he wanted me to move in with him and that
if I didn't want to I wouldn't need to work. I kept staring at him and he
continued, "Also I have several rooms here. I don't expect anything in
return right now or every really. I want your love not sex as payment or
anything. Sure I want to love you and sleep with you but that will come
whenever you want it, no pressure. Ok?" I smiled and said ok.  "I'm not
sure where this is going to lead but I'll stay home for now, take care of
the house, cooking, etc. Just like any other wife!" I said with a
chuckle. Rob smiled and we gathered up as many bags as we could and headed
upstairs. As we got to the top Rob told me there were 4 guestrooms that I
could choose from. I looked at him and asked him if there was room in the
master bedroom closets? He was surprised but said sure, there were 2
closets and he only used one. I smiled and said I would be honored to use
the other then. He smiled as he led me into the master bedroom. It was
spectacular. It had the bed of course, with a sitting area with a small
couch and 2 chairs situated around a fireplace. There was a sliding glass
door that led out onto a balcony overlooking the backyard. Off to the left
was a doorway that Rob led me through. There was another door on the right
that led into a huge walk-in closet. It was totally empty with a dressing
table, chair, mirrors and dresser along with all sorts of shelves and
racks. I stood shocked as Rob deposited the bags he carried and excused
himself so he could get the others. I left the closet and proceeded into
the bathroom. I noticed another door and saw the other closet. The bath
itself was everything you could want. It had 2 sinks, a very large tub that
looked like it could hold 4 people, a shower and of course the toilet. I
went back into my closet and proceed to put things away. Rob returned with
the rest of my bags and I asked if it was ok if I organized my things
alone. "I sort of need time to adjust and soak all this up if you don't
mind" I told him. He agreed and told me he would go downstairs to relax and
order us some pizza for dinner if that was ok. I told him that was fine.

I began putting things away not quite fully comprehending things but
knowing that it was so right. After getting everything in it's place I
picked up all the tags, bags and such and put them in the wastebasket I
found in the bathroom. I went back into my closet, although now I was
thinking of it as my dressing room since it was so large, had a vanity and
even a window. I went over and stood there staring out the window, watching
some golfers on the course behind the house. I finally decided I had better
get ready for dinner. I went back and took down the shortest black skirt we
had chosen and long with a red blouse. I set them aside as I opened my
drawers and took out a red bustier, nylons, and red panties. I stripped
down and examined myself in the mirror. I stripped off my makeup and began
reapplying, beginning with the edges of the breast-forms then proceeding to
my face. When I had it just the way I wanted it I slipped on the bustier
pulling it up and over my breasts. It was a perfect snug fit. I slid the
nylons up one leg and attached them to the garters, then repeated with the
other. I then slid on the panties, tucking myself back and up between my
legs, pushing my small balls up inside me slightly. I then put on my red
blouse and then slid the skirt up my legs, tucking the blouse in when I had
it in place. Yes it was short, just barely hiding the tops of my nylons,
just perfect for tonight. I walked over and took the black pair of 4" heels
and slipped into them. I went back to the vanity and sat down. I selected a
plain short gold necklace and fastened it around my neck. I found a
matching bracelet, which I fastened around a wrist, applied a light amount
of perfume and decided to head downstairs.

As I entered the family room, Rob let out a gasp. "God Diane, you are so
beautiful" he exclaimed. I smiled and sort of jumped as the doorbell
rang. He smiled and told me perfect, that must be the pizza. I smiled and
told him I would take care of it. He handed me some money and I headed for
the front door. I was nervous as I opened the door but the teenage delivery
boy was probably more nervous as he stammered he had a pizza. I smiled at
him as I took it and handed him the money. He began searching for change
when he dropped it all. He dropped to his hands and knees hurrying to pick
it all up. I knelt down and began picking up change for him when his hand
rubbed against my knee. He jerked it back so fast you would have thought I
was a leper. He face turned 3 shades of red as he stammered out an
apology. I told hi there was no need to apologize and handed him the money
I had collected from the floor. I told him not to worry about the change
that it was his tip and leaned forward and kissed him on the cheek. I
didn't think it was possible but he turned even redder. I smiled as he
thanked me and shut the door behind him. I collected the pizza and headed
into the kitchen. Rob was waiting and smiled as he asked if I now realized
how beautiful I was. I laughed and told him I supposed so but young horny
teenagers were no real test. We laughed together as we sat to eat the
pizza. We ate, sipped some beer and chatted about things we liked and
disliked. It's amazing how much we had in common. Now don't get me wrong,
we are very different but yet we like similar things so that I knew we
would enjoy life together.

When we got done we headed back to the family room and sat down to see what
was on TV. Rob sat at the end of the couch and I sat in the middle leaning
into him. He naturally draped his arm around me and I fit snug against him
as he surfed the channels. We finally settled on a movie we both enjoyed
and watched it as Rob caressed my arm and shoulder and played with my
hair. As we watched the movie I turned my head towards him to say something
but our lips met and opened in a long sensual kiss. I raised my arm around
his neck as he pulled me close. We continued our kiss for an eternity until
we finally broke away, breathing heavily. I could see the love and lust in
his eyes and I knew he could see the same in mine. I sat up slightly as our
bodies joined our lips in another embrace. As we kissed our hands began
roaming over one another, caressing each other. Rob's hand found my breast
and I was shocked by the feeling. Even though it was just a breast-form I
could feel his every touch and when he played with the nipple it sent shock
waves through my body. I was so turned on as I lowered my hand to his groin
and began stroking him through his pants. I could feel his cock so well and
I was dying to get my first look at it. I broke away from our kiss, smiled
longingly as I fumbled to get his pants unzipped. Rob helped with the belt
and hook, and lifted his hips as I pulled his pants and underwear down. His
beautiful cock sprang into view. Now since Rob is a tall man I could now
see all his proportions where correct. Although nothing for the record
books, his cock was still much more than average. It looked to be about 8
inches long with a slight curve to it but with a width that surprised
me. The few cocks I had previously seen were what I would consider normal
length and width. Rob's was VERY wide. Without actually measuring it, it
looked to be about 4" in width, which was much wider than any I had seen
before. I slowly lowered my head until it was right in front of me. I began
by licking the tip of the head. Rob moaned as I began licking it and the
cock began twitching. I reached out with a hand to hold the base while I
sucked on the head a bit. Rob began moaning more, telling me how good it
felt and that he would probably cum fairly quickly with me sucking like
that. I continued to suck on it, letting a bit more slowly enter my
mouth. There was no way I was going to be able to suck it all the way in
but I was determined to get as much in as possible. While I was doing this
Rob began playing with my ass. Since I was half lying on the couch, Rob
could easily reach it. He raised up my skirt, lowered the back of my
panties and began fingering my ass. I squirmed and moaned as I sucked more
and more of his cock into my mouth. I would bob my head up and down on it
slowly, taking slightly more of it every few seconds after getting used to
what was already down my throat. I kept this up for quite a while, or at
least it seemed like it, until I had about half of his cock in my
throat. By this time Rob had three fingers loosening up my ass and I could
feel his cock beginning to stiffen and his balls rise up a bit. I prepared
myself not knowing how much this beautiful cock would pump into me. It's a
good think too, because either Rob cums a lot or he has been saving it up
because I had to keep swallowing 6 times to keep from overfilling with his
wonderful cum. Even so, a little dribbled out of the corner of my
mouth. When he was finished I licked up his still hard cock, cleaning it
all up. I looked up at him and wiped up the leftover cum off my face and
licked it off my fingers. Rob smiled and asked if I enjoyed that, cause he
sure did!  I told him I sure did and asked if he always came that much. He
told me that he has always cum a lot but that he can't remember ever having
cum that much, it was just so good for him. I smiled back while I squeezed
my ass around his fingers. He continued stroking his fingers in and out of
me while I stroked his cock back to life.  As he returned to life, Rob
removed his fingers from my ass and told me to stand up. I reluctantly
stood up and as I did Rob reached out and pulled my panties all the way
down. As he stood up I stepped out of my panties. Rob then swept me up into
his arms and carried me upstairs. No for all you girls out there, if you
have never been carried you are missing out on one of the biggest thrills
in your life. It feels so wonderful, sensual, totally at someone else's
control to be carried like that. Needless to say, at that moment I knew
what was going to happen and that I never ever wanted to be anywhere else
in my life. I knew then that Rob was the man meant for me. When we reached
the bedroom he stood me on my feet and proceeded to remove my blouse and
skirt. He left my bustier and nylons on as he removed his socks and
shirt. I stepped out of my heels and into his arms. We embraced with a long
sensual kiss as we climbed into bed lying side by side. His hands roamed
over my body caressing me, getting me more and more excited. I rolled onto
my back pulling his cock towards me. He rolled over onto me, between my
legs that I spread wide. I pulled my legs up a bit as he moved into
position. With the head of his monster cock touching my entry he leaned
forward to kiss me. We kissed long and hard as he began pushing his way
into me. To Rob's credit he began by entering oh so slowly. It was like
nothing I had ever encountered. There was pain but more than that was the
feeling of being stuffed to the max. Me managed to get about halfway in or
so when he must have lost control because at that point he roughly rammed
the rest in me. I gasped loudly as his balls slapped up against my rear. I
felt like I was on fire for a moment but Rob slowed down and as we caught
our breaths the pain subsided a bit to be replaced by that unbelievable
fullness. I pulled him down to me to begin a full sexual kiss, our tongues
dancing with one another. Rob again began to move, sliding his cock about
halfway out before returning the full length back inside me. I had
recovered from the initial shock and weakly wrapped my legs around Rob's
waist. I tried to squeeze my ass muscles around him as he pumped in and out
but with his wide cock I'm not sure how much I was actually squeezing at
that point. I could tell he was about to cum as he picked up his pace and
the look on his face conveyed pure ecstasy. I whispered to him "Cum in me
baby, make me your woman". That must have triggered him because he began
spurting deep inside me with long hard strokes. I could feel his cum splash
up inside me filling me like I had never been filled before. As he slowed
down I could feel some of his cum begin to seep out of me. Damn I thought,
how much does this guy cum? A lot I hope! Rob lay there on top of me with
his softening cock still inside me and my legs wrapped around him. We
kissed and stared into each others eyes for several minutes before he moved
up and off me. I felt a huge disappointment as his cock slipped out of me
but I knew that it would return home before long! I got up and went into
the bathroom to clean up a bit. I went into my closet and took out the
short baby blue nightie and slipped it over my head. I returned to the
bathroom to get a wash cloth, wet it with some warm water and a bit of soap
and returned to the bed. Rob was lying there with a content look as I sat
beside him and washed off his cock. He started to protest but I silenced
him by telling him I was just doing what any woman should do so just lay
back and relax. When I was done I rinsed out the wash cloth and returned to
cuddle up next to Rob. Lying on my side with Rob firmly up against my back,
his cock semi-hard against my ass and his hand cupping my breast I relaxed
and fell into my first wonderful night's sleep as Diane, fiancé to Rob.

End of Part 1.

This is the end of my initial attempt at wiring about my experiences. I
would like to hear from people out there. If people enjoy this then I will
put more down into words.

Dianenctv@yahoo.com