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The Lady Is A Tramp
by Doingbothways (doingbothways@yahoo.com)

***

A coming of age story of a crossdresser turning 
transgender. (tg, cd)


***

What is a tramp, what is a lady, I do not know but I 
seem to fit into both of the general public's way of 
thinking. I do not have a problem with that at all. I 
love it. You ask who I am to say these things. I am 
five foot 6 inches tall and weigh one hundred and 
thirty pounds. Long brown hair, brown eyes and some say 
I have man made curves. My measurements are 35-28-36. 
There is one tiny secret. 

That I have not mentioned yet. I have a penis. What you 
ask your self did I just say. The lady has a dick. How 
did that happen you ask well it was simple? Many years 
and a life time ago when I was a small little boy I did 
the normal things little boys do. I also have three 
sisters. Two sisters are older and one younger sister. 
We spent the summers on our grandparent's farm. We ran, 
we swam in the pond and we just had fun all day. 

On this one hot and sunny day we ended up at pond and 
the girls always kept plenty of suits at the small barn 
near the pond. I did not have a suit to wear. Kathy my 
oldest sister said that there were several suits that I 
could wear and still have fun. 

I told her "No way," she just said then I would swim 
naked. I told her that was not going to happen. My hair 
was longer than most boys. It was the seventies and 
everyone had longer hair. I found a pair of bottoms 
that were blue with white stripes on them and put them 
on. They were close to my size, maybe a bit smaller and 
they seemed to be tight on my butt. 

I walked out of the barn and the girls started to laugh 
at me. They were laughing but not at me but the fact 
that I did not have the top on. They told me to put it 
on and then come back. I was nine or ten years old then 
what could I do. I found the top and put it on. I 
walked out and began to have fun swimming and having 
fun. 

It was later in the afternoon that a group of kids from 
down the road came to the pond to cool off from doing 
there chores. It did not seem different as this was the 
only swimming pond for miles around. We had been there 
before when kids would stop by and today was no 
different.

Well, if you consider that as a nine year old boy is 
wearing a two piece girl's bathing suit. It did not 
seem any different. We swam and dived off the rocks and 
there was a tree with a rope tied to the branch that 
over hung the waters edge. The other kids did not 
notice that I was different or for that matter care. 
Everyone knew that our grandparents that a lot of grand 
kids that visited threw out the year and holidays. 

We were the only ones that stayed the entire summer. 
Our cousins had already left and we had the place to 
out self's for the rest of the summer. After a while a 
car drove up and what appeared to be parents of some of 
the kids walked over to the sandy area and started to 
talk to some of the kids. We were all standing around 
and having fun and it was then that the mom remarked 
that there were so many girls out today and will make 
sure her son comes by tomorrow with cold drinks for 
everyone. 

The day came to a close and we all changed out of our 
suits and headed back to the house for dinner. The 
following days were hot and we always ended up at the 
pond. My sisters found a new way to torment me. They 
insist that I put one of there suits when I am with 
them. The summer is fading fast and that is when the 
not so fast fading suntan lines could be a problem as 
little boys do not have tan lines that cover there 
breasts and high up on the thighs. I will have to wait 
to see how that goes. 

As the summer comes to an end and we head back to the 
cold winter of the north. That following October my 
sisters decided that for Halloween we would all dress 
as witches. I have never seen a boy witch before. When 
I asked her about boy witches she just said that it was 
no big deal that it would be fun. What I found was we 
were all going to be girl witches. My sisters insisted 
that I keep my long hair and what ever hair I had under 
my arms had to be shaved as well as any hair below the 
waist area. 

My oldest sister Kathy began to practice putting makeup 
on me. At first it was just a small amount then as 
Halloween came closer it was more and much more normal 
looking. The week before Halloween Kathy wanted to test 
out the makeup and see how the entire effect was. What 
took place was having Kathy gather clothes from my 
youngest sister Jan. The clothes were a bit tight and 
Kathy insisted that I wear Jan's panties and bra, the 
bra needed a bit of padding to fill it out. Lucky Jan 
was small in this area. A pair of jeans and a top was 
all and a different hair style and off we went. 

I did not know it was off to the mall. At the mall it 
was looking at clothes and trying them on. Bluejeans 
and tops. The jeans were a bit tighter on me and a lot 
lower on my hips. The tops were more colorful. We 
purchased the outfit and off we went. It was to a 
beauty shop and new hair and makeup. We went to the 
food court and Kathy insisted that I sit alone and say 
nothing. I did just that. 

While eating my hamburger in came my other sister and 
her friend and they all sat down. When they stood up 
they walked over to me, or should I say they walked in 
my direction, they walked right past me. Kathy turned 
around and said Hi to me, it was then that the other 
two turned around and walked back towards me. Still not 
knowing it was me. It was when Kathy asked me to join 
them shopping that Mary my middle sister asked what we 
were looking for and Kathy just said nothing and 
everything, what ever was on sale. 

We all went into a department store and Kathy was 
looking at dresses. She handed me a dress and told me 
to try it on. I went to the back of the store and the 
dressing room was more of a room were you tried on 
outfits and there were several ladies there trying on 
clothes. I stood there and changed into the dress and 
stood there. Kathy called Jan in and asked her what she 
thought of the dress. Jan said that it was a bit short 
for me as I was only rather young. Kathy agreed and 
told me to change again. 

I lifted up the dress up over my head and stood there 
in a bra and panties. That is when Kathy told me to 
lower my panties a bit to show Jan what was under them. 
I slid them down a bit and when it was apparent that 
there was something that should not be there was there. 
Jan then said is that you Charlie, I said yes. Jan came 
over and hugged me and looked me over and turned me 
around and that was it. I dressed and we all left. 

Halloween had came and gone. No one knew who I was and 
everyone just thought I was on of the sisters. That 
winter Kathy was off to college and we all waited for 
summer to return. Our parents started to disagree a lot 
and even yelled at times. The summer could not come 
fast enough for us kids as the friction between our 
parents was intense. When summer came Kathy came to 
visit us. It was the same as before, dress up that is. 
We called it a game and that was all. I did enjoy 
wearing the swim suit again, two piece that is. 

Towards the end of summer Kathy was back at school and 
we were off to the big city and school. Kathy has 
finished her second year of medical school. The 
following summer was different for all of us. Mom and 
dad had split up and grandma had past away. The 
following summer just me and Jan that went to the farm. 
By then things have changed. My mental and physical 
being was different. I talked to Kathy about some 
changes I was having and she told me she was some what 
aware of them as she knew it would happen as she had 
been providing the family with vitamins. She said that 
grandpa would not notice that there were two girls 
instead of one. 

Kathy began to tell me that what was happening to me 
was at first fun but know it was the real thing. She 
said that the shape of my hips was no joke and the 
growing breasts were real. She even knew that my boy 
parts had stopped growing and even maybe grew smaller. 
She said that I was now going to be a girl. I did not 
resist or go crazy. She also explained that the 
vitamins contained a drug that affected my mental side 
and reduced my stress as well as being a calming agent 
and several other things that I did not understand at 
the moment. From that moment on I was a girl. 

When summer came to an end Kathy had convinced mom to 
let me live there and to attend school there. Grandpa 
had no clue. Kathy stopped by a couple times during the 
winter and we talked and she added some injections for 
me and things started to change a lot faster and in 
greater detail. I saw mom about twice a year and 
dressed as a boy for the visits. Several years have 
gone by and mom has moved away by herself and dad has 
not been heard from in quite a while. Kathy still 
visits and talks to me a lot. 

I have lived as a girl for years now and even graduated 
high school as a girl. 

**

Kathy is in her last year of residence training. She 
invited me to live with her and figure out what I 
wanted to do. I told her college and then who knew. She 
told me that if I wanted to step it up that she could 
arrange to complete a breast enlargement for me. 

I agreed and thought what the heck. At the hospital 
everyone thought I was a woman. The operation was 
great. I look down and see a pair of perky larger 
breasts. An ample 34c or a tight 36b is what I have 
now. I have taken the female hormones now for many 
years and the results are clear. Slim waist and round 
hips as well as shapely legs and a near hair less body. 
Several years have gone by and it is just so normal to 
be this way, Kathy has been a great help in all of 
this. I did decide to go into the restaurant field. 

I have been working as a hostess and sever as well as 
designing the menu and running the kitchen. There has 
been no steady dating or affairs as I have been very 
busy getting on with learning what that is I want to 
be. I know that being a woman is number one. I have had 
real plan yet as to what direction I will go. I did 
realize that at the present kids are not in the plan. 
Kathy had told me of a procedure that mimics a full 
castration. 

The operation is reversible if I so desire, that was 
Kathy idea as one never knows. What took place was 
creating a place up in me to move the testicles to then 
removal of the ball sac and then getting additional 
hormone injections into the penis for several months to 
reduce the size and then placing what was left of the 
penis under the layer of muscle and allowing only the 
opening poke threw. With just a small landing strip of 
hair there my penis is all but gone, I have been seen 
naked and no one could tell. 

I think back at my first couple outing with guys and I 
can say that if I did not want them to know, they never 
did. Know one encounter lasted very long. If one did 
take the extra effort to allow me to do my thing then 
the rewards were in his or her favor. I remember the 
coffee shop guy with great thoughts. He was wonderful. 
I was not bad either. It started innocent enough. I 
would get my coffee every morning he would smile and 
after a while we would chat and tease each other. 

One day I was taking a day off and going to the beach 
to get some sun. I was wearing a pair of boxer style 
shorts and a pair of tennis shoes and I had on a wife 
beater style t-shirt. It was white and fit close to my 
skin and hugged the curves. I had tossed on a light 
nylon windbreaker. It was not zipped up. I went into 
the coffee shop and walked up and he knew what I always 
ordered and proceeded to make it when he saw me walk 
in. 

I went to the counter and it was then I sensed that he 
was looking at my chest and not looking at me. While he 
was getting my change I glanced down and realized my 
nipples were very visible under the fabric as well as 
the roundness and fullness of my breasts. I was at 
first stunned then felt a little naughty. I knew he was 
looking and I chatted with him as long as I could until 
the next customer came in. I smiled and walked out. I 
thought about it all day at the beach. Several days 
later I decided to turn up the heat. 

I wore the sexiest bra that pushed it all up and out 
and left a hint of nipple showing. I put on a loose 
button up blouse and made sure that cleavage was there 
as well a as view to die for. I waited until it was 
almost empty and then I walked in. When he saw me he 
began to fix my coffee. Standing there at the counter 
we chatted while his back was to me. 

When he turned around I insured he saw an eye full as I 
had made sure the buttons were undid enough to see it 
all and with a little opening the blouse up it was no 
confusion he was looking and when I told him that my 
eyes were up here and he said sure they are but what is 
down there is also very nice to look at. I laughed and 
took my coffee and walked out. I know he was smiling 
and I was thrilled. The next day I wore a pair of ultra 
low rise jeans and a knit top. I also had on a pair of 
bright pink thong panties. 

I walked in and as usual he started to get my coffee. 
We chatted for a minute or so and then stepped back and 
asked if these jeans made my legs look short. He leaned 
over the counter and looked down. I had adjusted the 
jeans just before I asked him knowing they were showing 
the top of the panty up front and when I turned around 
he saw not only the pink triangle of fabric, but the 
top two inches of my butt cheeks. I turned around and 
he said the jeans made my legs look great and not to 
worry about it. 

I smiled and walked out. 

**

The following week I wore the shortest skirt I could 
find. The skirt was made of jeans fabric. So off came 
several inches with the scissors. One washing and when 
I put it on it did not seem short enough. So off came 
more. Washed again and then they were short enough. So 
short I knew with just a little adjustment my butt 
would be seen. So the next day I wore it into the 
coffee shop. Even at first he looked and saw it was 
short. It was standing in line that I hiked it up and 
asked him if the skirt was too short. 

He again leaned over and said no, but I turned around 
and he only said that it was hard to tell. So I hiked 
it up showing so that not just a peak of panties was 
but damn near my entire ass was in view, I turned 
around got my coffee and walked out. While walking out 
I made sure it got hiked up real high to allow him a 
parting view. 

That was the way we started our romp. I knew that the 
green car in the parking lot was his so I decided to 
leave a small hint. Well size 5 hint in yellow and red 
lace pair of thongs. I put them over his rear view 
mirror, that way he was sure to see them. I guess the 
note I attached to them did not hurt either. The note 
was just an address and a time. It was up to him to 
understand what it all meant. I was sure he had an 
idea. 

I went home to get ready and let the night begin. I 
keep a neat and tidy house, I guess the truth be told 
darn near spotless. I had enough cold beer in the 
fridge and mixed drink items to ensure a relaxing 
evening. I had put on a pair of matching bra and 
panties. I slipped on a wrap around style dress, deep 
cut and short. I now just needed to wait. My wait was 
not long there was a knock at the door and I waited a 
minute, did not want to seem I was in a hurry. 

I opened the door and there he stood. He even picked up 
a small bouquet of flowers. I put the flowers in a vase 
and handed him a beer. We sat down and exchanged words 
and just general talk. I excused myself to get some 
chips and dip and made sure my dress was a bit untied 
and revealed my cleavage and thighs. We talked and sat 
closer and exchanged a kiss or two and then a full head 
on swap spit kiss. His hands were all over me and I was 
not stopping him. I again excused myself and told him 
to get comfortable. 

I returned to the living room wearing only my heels and 
bar and panties. I reached for him and as he stood up I 
began to unbutton his shirt and pushing it over his 
shoulders. With it on the floor and I was starting on 
his jeans. They fell in a pile and he stepped out of 
them with ease. I tugged on his boxers and they also 
began a downward direction. All the time he was 
starting to sway and get excited. That was an easy 
thing to see, his now growing member was coming to 
life. I had him sit down on the couch while I kneeled 
between his legs and began to kiss every where on his 
thighs up to his now fully erect member. 

I grasped the base with my hands and began to rub and 
stroke him while he was starting to rotate his hips and 
slid down a bit. I was kissing his now much enlarged 
head on his member and that was the area of my concern 
and passion. I was running my lips over it and began to 
take it in. I was turning my head as well as going down 
and up and up and down. 

He was now rocking and I was rolling and it was good. I 
could feel the tightening of his skin and then a 
smaller thrust followed by a larger thrust and then a 
still larger thrust. I could feel him tighten and arch 
his back and then a thrust and the reward was there as 
he spilled his juice in to my now juicy throat. I stood 
up and he had this look of totally at ease. I excused 
myself and returned to the kitchen for fresh drinks. I 
entered the living room and he had his boxers on. I 
looked at him and said what is wrong a girl can not 
take a break and continue the fun. 

He laughed and we sat down and relaxed with the new 
drinks. We kissed and I whispered in is ear that I was 
going to make his dream come true. He asked what dream 
I told him the dream of doing a girl in the rear. He 
looked up and the smile was all I needed for the 
reaction I was seeking. We started to kiss and then his 
hands were now stroking my breasts, I was happy that he 
was happy and that he was feeling what modern science 
can create and enhance. I was now developing his man 
hood to an erect status again. 

He was starting to get in a rhythm at that moment I 
reached over and took a tube of lube and began to apply 
it to my neither regions. When I felt that I was ready 
I reached over to him and moved to the floor and while 
I was getting into the doggie position he was pulling 
down my panties. I kicked them off and spread my legs 
apart. He inched closer and closer until I could feel 
his shaft touching my rear cheek. I reached back and 
helped him find the spot that he was looking for. I 
felt him penetrating me and going deeper. I was soon 
feeling the fullness of him inside me. 

I was soon matching his strokes and his rhythm, it was 
pure lust. He was picking up speed and pushing harder. 
When he was deep inside he would push even harder and 
wait a moment to withdraw. The intense pressure was 
pushing me over the edge. When he came I could feel the 
warm gush of his fluids enter me. The evening was 
complete. 

On Monday morning when I walked into the coffee shop he 
was there and as usual created a great cup of coffee 
for me. I asked him when he handed me my change that 
what does a girl got to do to get a free cup of coffee.

END

* * * * * * * * * * * * * * * * * * * * * * * * * * * *
It's okay to *READ* stories about unprotected sex with
others outside a monogamous relationship. But it isn't
okay to *HAVE* unprotected sex with people other than
a trusted partner. 4-million people around the world 
contract HIV every year. You only have one body per 
lifetime, so take good care of it!
* * * * * * * * * * * * * * * * * * * * * * * * * * * *
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