Brooke free porn video

I was 27 years old when I decided.

I had been married to a very pretty woman by the name of Mandy for 3
years. She was about 6 years older than me and very much into her
‘career’. She traveled a lot in her business and most of it took her to
the city her parents were retired in. What that meant was that there were
many times when she would go on a business trip and then spend the weekend
with her parents and then work in the same city the next week. It also
meant that I had about every third weekend to do whatever I wanted.

The Beginning

Ever since I could remember, I had felt ‘different’. As a c***d I always
felt more comfortable with girls than other boys. As an adolescent, I
participated in sports and was pretty good but I always wanted to be a
cheerleader. I used to go into my parents’ room when I was alone in the
house and put on my mom’s clothes. I was so ashamed of what I did and
while I did get aroused by wearing women’s clothing it also felt
‘comfortable’. Sometimes I would even try some of her makeup but always
washed it off and put everything back where it belonged.

I thought I was a transvestite but there was always the feeling that
somehow I was not really a boy. When I was very little, I would pray to
God at night to please change me to a girl. When I watched movies or the
television, I would imagine myself to be the lead female role. The first
time I saw the Star Wars movies as a k**, I wanted to be Princess Leia
especially when she wore that costume in Return of the Jedi. When I was in
middle school and the girls bodies started changing I was so jealous of
them.

Mostly I just pretended to be a normal k**. I was a good athlete and
played baseball, football and basketball. I got my height early and I was
5’8′ by the time I was in 7th grade. I had really strong legs and a pretty
large butt for a boy but my dad always said that was why I was so fast.
However, my dad was 5’10 and my mom was 5’2′ so I never grew after that. I
was good enough to play in high school but once I graduated, my sports
career was over.

I dated one girl all the way through high school. She was the Homecoming
Queen and very popular. She was nice and had lots of friends. We used to
have some very hot make out sessions and we used to mutually masturbate
each other to orgasm. We started having sex our senior year but I
sometimes had trouble. I secretly wanted to be her sometimes and it used
to just really fuck with my head.

After high school, we ended up going our separate ways. I went to college
and she went to beauty school. Even then I wanted to be her but I came
home during freshman year and she was already dating someone else. We
talked on the phone a couple times and then had coffee a couple times and
parted as friends. She told me her new boyfriend was a ‘real man’ and that
he sometimes made love to her 2 or 3 times a night. I told her I was
jealous and she smiled and said, ‘Of him or me?’ and I blushed and smiled
but never answered.

My dad was named Mark and my mom was named Ellen. They were both still
very conscious of their appearance. They watched their diet and my mom did
yoga. They both had sort of ‘mousy’ brown hair with my dad being a shade
darker. Dad had hazel eyes and mom’s eyes were blue. I had inherited their
brown hair and my mom’s blue eyes. They were very still both young even
though they seemed old to me. Mom told me once that I was conceived on
Prom Night their senior year. They got married right after graduation and
I was born 6 months later. My given name is Jerry but if I had been born
a girl, my mom told me she was going to name me Brooke. Dad was a
construction worker and ran heavy equipment and mom worked retail. I was
an only c***d and we had a nice life. I never told either of them about my
feelings as a k** because I just didn’t think they would understand. They
were both kind and tolerant but they were also very traditional.

After high school graduation, I went to the State University where I
worked and went to school. It was during this time I began to buy my own
female wardrobe. At first, when I lived in the dorm, it was only a few
pairs of panties that I would sometimes put on when my roommate wasn’t
around. I even wore them under my boy clothes sometimes to class or even
to my job as a janitor in a shopping mall.

They made me feel sexy and naughty and normal if that makes any sense. I
loved they way the felt so light and airy. Sometimes I would tuck my boy
parts back between my legs and put on a pair of panties and look in the
mirror. While my strong legs from being an athlete in high school were
still a little ‘thick’ for a boy and my butt was kinda big for a boy, I
was beginning to be not so defined muscles because I wasn’t working out
anymore. Sometimes when I did this I looked like a girl from the waist
down.

After my freshman year, my roommate Zack and I decided to get an apartment
together. We found a place not far from campus that had two bedrooms and
two bathrooms and it was mostly furnished. We got along okay, probably
because we each were pretty independent. He had a girlfriend and so did I.
He ended up spending a lot of time with her and when my girlfriend and I
were together we were alone a lot. We had sex but it was never ‘rock my
world’ sex and I occasionally had trouble maintaining an erection. It was
the same problem, I wanted to be her not me.

My female wardrobe was growing though a little at a time. I now had
several matching bra and panty sets. I also had a pair of girl jeans that
seemed to almost fit better than my own jeans and a denim mini skirt and a
couple pastel tees and one yellow sundress. I also had several pair of
stockings and some garter belts and some assorted tights and panty hose. I
also had a pair of inexpensive breast forms. I bought an inexpensive make
up kit and a cheap platinum blonde wig.

I kept all this under lock and key in a foot locker in my closet. While I
sometimes wore the panties and bras under my boy clothes, I only got
completely dressed when my roommate was home on break. I had to stay there
over breaks because of my job. I never went out but I would get dressed
and then sometimes go online and pretend to be a beautiful, sexy woman in
some of the chat rooms on websites.

This lasted for a couple of years. I broke up with my girlfriend during
the fall of my junior year and that was the first time I ever shaved my
legs. O…M…G! I loved the way it felt and I kept them shaved all winter. I
also sometimes would go to a grocery store and buy a couple of bottles of
Nair. Then I would go home and within minutes I would be bald as a baby
from the eyebrows down. The only problem was that I had to stop around the
end of February so that all my leg and body hair would grow out by the
time it got warm.

The fall of my senior year, things began to change. It had started to get
cool again and it was jeans and sweater weather. After class one day I
went to the store and bought a couple bottles of Nair and went home and
removed all my body and leg hair. Then I went online. For some reason, I
decided to place an ad. I wanted to meet someone. I was tired of dressing
and fantasizing about being with another man. I wanted to explore and see
what it was really like.

I didn’t have any pics and so I didn’t get much response. The next Monday,
I opened my email and there was a notification that I had received a
response so I followed the link to the site. It was from another trans
person named Sherri. She was from another city but occasionally traveled
to our area. She had attached a photo and looked semi passable but dressed
in a ‘cheap’ manner. My hands were shaking as I typed a response. Over the
next several weeks we exchanged many messages and eventually emails. She
wanted to know my ‘fem’ name. I wrote her back that I went by Brooke.

After a couple of months, we agreed to meet. Sherri was going to be in the
city south of my college town over one of our winter breaks. My wardrobe
had expanded a little more by now. I was a size 10 because I still had
male muscle mass. For our ‘date’ I picked a salmon colored skirt suit
along with a very pretty blush colored sleeveless top with a scoop neck.
The skirt came to just about 2 inches above my knees. Matching bra and
panty set along with nude thigh highs and salmon colored 3 inch pumps. I
had also bought a better wig that more closely matched my natural hair
color. It was shoulder length with bangs and some highlights running
through it. We were going to meet at her hotel then go out to gay bar
that featured a ‘drag show’ on Saturday nights.

I was so frigging nervous I almost didn’t go. But about 4 that afternoon,
I took a hot bath with some scented oil and some candles. I shaved every
square inch of my body and then patted myself dry. It was break so I
didn’t have to worry about Zack walking in. I went to my room and began to
dress. First I took some flesh colored medical tape and pulled the flesh
on my chest from one side and attached it to the other side. This gave the
appearance of real cleavage and even with inexpensive breast forms made me
feel fem. I put on my matching burgundy colored bra and panty set. The
panties had a lacey insert and were bikini style and the bra was size 40
‘B’. I drew the panties up my hairless legs which gave me an erection. I
relieved myself into a tissue I took from my nightstand and then ‘tucked’
my boy parts back between my legs. I fastened the bra and then turned it
around to put my arms through the shoulder straps. I inserted my breast
forms and then went to the kitchen to get a glass of wine.

Then I went back to my bathroom with my makeup kit. I had shaved as close
as possible but as a brunette, I still needed concealer. I went slowly and
carefully. I wanted to look good but I also enjoyed this part of the
process. I had several women’s magazines under my mattress and had spent
hours on youtube watching makeup tutorials. I had decided to do
understated evening shades and colors that went with my natural tones.
Once I finished I went back downstairs for another glass of wine.

It was now about 6:30 and I didn’t have to leave until 7:30. It was going
to take about 45 minutes to get to Sherri’s hotel and the show didn’t
start until 10:00. I had two glasses of wine already so I put on a short
pink lace robe and went downstairs to watch a little television. At about
7:00, I went back up to my room and put on my outfit for the evening. I
was feeling very sexy and fem by now and when I put my wig on and brushed
it out, I looked in the mirror. Brooke looked back at me and I felt very
calm and ‘right’. I then put on some red ‘press on’ nails and put my
wallet in my purse along with some money and a few necessities like lip
stick and compact. I took one last look in the mirror and walked to the
front door. Fortunately, our apartment was on the first level and our door
led to the outside. I walked over to my little Honda Civic and opened the
door. Hearing my heels click on the pavement, wiggling my panty clad
bottom as I walked, the act of sitting while smoothing my skirt and
swinging both my legs into the car at the same time gave me a sense of
excitement and joy.

I got to Sherri’s hotel and called her mobile. She met me at the door and
we embraced. I went in and we sat with another glass of wine and talked
like two girlfriends who hadn’t seen each other in a month. I was in
heaven. From how I was dressed to the lipstick imprint on my wine glass, I
was totally Brooke. At about 9:30 we decided to head out. We both had to
pee and of course I sat and felt very fem. Sherri drove in her company
car. We stopped at a light in the left turn lane and a car pulled up next
to my side. I felt eyes on me and looked over. There was a young guy in a
beat up Chevy and he looked over at me and smiled. I smiled back and then
the light turned green leaving my new ‘boyfriend’ at the light.

We got to the bar and went to the main door. There was a $5 dollar cover
charge and they checked ID. The guy at the door must have been about 6’5′
and was a total muscle head. He looked at my Jerry ID and then back at me.
He smiled down at me and said, ‘Have fun pretty lady.’ I almost melted. We
went inside and Sherri ran into some other ‘girls’ she knew and we sat
with them right by the dance floor. I ordered another glass of wine. We
all chatted and laughed and then the lights went down and the show
started.

The MC came out and she was an obvious ‘queen’ but very funny and then
they had a few acts with a ‘Shania Twain’ impersonator and a chorus line.
Second up was a ‘Cher’ and then a ‘Madonna’ impersonator came out and did
the grand finale. The MC came out and did a little more comedy and then
the first show closed. In between sets they played dance music and a
couple of the girls at our table got up and danced and I saw Sherri look
at me and then suddenly I felt a hand on my shoulder.

It was the guy from the front door. ‘Wanna dance?’ and he stuck his hand
out. I looked back at Sherri and her eyes got big and she motioned to go
ahead. So I put my hand with the long red painted nails in his and we made
our way to the dance floor. The first couple of songs were fast and I had
just enough alcohol to allow me to be totally Brooke. I felt sexy and
feminine and alluring. Then they started playing slow dance songs and my
mystery man took me in his arms. ‘What’s your name?’ He asked. ‘I’m Brooke
and you are?’ He said his name was Mike. We danced and talked. He
commented how had never seen me here before and hoped I would come back.
‘We need more girls who actually look like girls here.’ which I took as a
compliment. He wanted to know if he could see me again and I told him I
was with someone. He said, ‘Lucky guy.’ By now I could feel his very hard
cock up against my tummy as we danced and I felt a tingle in my panties as
well.

The last song ended before the second show started and Mike e****ted me
back to our table. The MC came on and the second show was a little
raunchier than the first. The MC interacted with our table and during one
‘rif’ she said, ‘How come you bitches brought a real girl with you?’
Suddenly the spotlight came on me and I was terrified. Sherri piped up
with, ‘Hey, he’s with me.’ And everyone laughed. The MC looked at me and
said, ‘Sorry sweetie. But was you always ‘fish’?’ With that everyone
laughed and the MC moved on. But eventually 2:00 hit and the place began
to close. Sherri drove back to her hotel and asked me in. At first I
declined and then she put her hand on my thigh, ‘Please? She said. So we
got out of the car and went in. I went in and peed while she poured more
wine. I freshened my make up and went back out. She did the same while I
sipped my glass of wine.

Sherri came out and sat next to me on the bed. She wiped away a stray hair
from my face. I was nervous but I looked up. She took my wine glass and
set it on the table. ‘You’re very pretty, Brooke.’ I was shy and smiled.
Sherri said ‘I mean it. Didn’t you notice all those other girls tonight?
They all looked ‘hard’. You were the one who tried to look like a woman.’
I smiled and looked at Sherri again. ‘Thank you. I’ve always felt somehow
different and tonight was really magical for me.’

Then Sherri leaned in for a kiss. I kissed back. Then we kissed more
deeply and I felt her tongue as it began to explore my lips and probe my
mouth. I felt Sherri’s hand on my thigh and we made out as her hand worked
its way under my skirt. Sherri paused long enough to whisper, ‘Touch me
baby.’ And so I took my hand and began to reach under her very short black
evening dress. Either she didn’t wear panties or she removed them in the
bathroom.

Sherri began caressing my pretty panties and then I felt her hand go
inside where she pulled out an organ I was wishing wasn’t there. Soon we
were kissing and mutually masturbating. It only took a few minutes for me
and I cummed and moaned like a girl. She stopped kissing and took her hand
and licked it clean. The she looked me in the eyes and said, ‘Ever suck
cock before?’ I shook my head. Her voice took on more authority, ‘Get on
your knees.’ I did as I was told and she stood in front of me and lifted
the front of her dress. ‘Suck it, bitch!’ So like a good girl I licked the
head and the drops of precum tasted salty. I kissed the head and then
licked all along the shaft. I worked my way up to her balls which were
salty and smelled like a man and then I took each one in my mouth and
sucked gently. Sherri rolled her head back and moaned, ‘Damn girl!’ was
all she said. Then I licked my way back up the shaft and took the head in
my mouth where I swirled my tongue around it. Soon I was bobbing up and
down on that dick like a pro with both of us moaning and sucking sounds.

I began to feel Sherri tense a little and then I felt her whole body tense
as she grabbed the back of my head and shoved her cock to the back of my
throat. I swallowed and swallowed again. I stayed on my knees and sucked
that dick until it went soft. Sherri laid back down on the bed and I went
in to fix my face which was a wreck. I did the best I could and came back
out and picked up my purse to leave.

While I had been in the bathroom, Sherri had taken off her wig and was
wearing boy jeans and a tee shirt. She was removing her make up in the
mirror. She topped and came over and kissed my cheek. ‘When will I see you
again?’ I said. ‘Oh…don’t worry, I’ll call you.’ And with that I left and
I knew I would never see her.

It was 4 in the morning and fortunately I was almost sobered up. I drove
back to our college town and took off my pretty clothes and wig and make
up. I put everything away in my locked foot locker and wished I could be
Brooke all the time. She was pretty and fun and confident and sexy and I
was ….me.

That spring, as I was letting my leg and body hair grow back, Zack
informed me that he and his girlfriend were moving in together. I
congratulated him and then helped him move. I decided against trying to
find another roommate and I talked to our landlord. He had a one room
efficiency that was furnished and we agreed to let me move there.

I didn’t have a girlfriend and had no real prospects so I ended up keeping
my legs shaved all the time now. I even gave myself pedicures and my toes
were almost always polished a very bright red or pretty hot pink color.
Even though it was summer, I wore jeans and I almost never wore my boy
underwear. I could hardly wait until fall when I could get rid of all my
ugly body hair.

I went to an ‘adult shop’ in the city to the south and I bought a very
life-like rubber penis with balls and some lube. It was almost 7 inches
long and about half the size of my wrist. Almost every night I would get
completely dressed and then drink wine until tipsy and go to my bed where
I had mounted the rubber cock on my bed post. I would suck it and turn
around and fuck myself on it. It hurt a lot at first but after I got used
to it and was a little ‘stretched out’ back there I found I could hit my
‘spot’ and I made myself crazy. I believed I was gay and I was very much
in the closet. I was getting a little flabby and sometimes I could feel
my ass and my thighs jiggle when I walked real fast or tried to run.

So my senior year came and went and I graduated. My folks came to town and
I had only seen them a few times over Christmas over the last 4 years. My
dad joked a little about how chubby I was getting and my mom wanted to
know if I had a girlfriend. I lied and told her yes. She wanted to know
where she was and I told her she was working but wanted to meet them soon.

The Middle

I looked for a job until I was worn out. I had a 2.7 overall GPA and my
degree was in communications. I would send resumes and not get job
interviews. I was still working as a janitor at the shopping mall when I
met Mandy. She was in town on business and we just happened to meet when
she spilled her drink in the mall. We made a couple of jokes and then she
left. She was back in town a few weeks later and she was at the mall where
I ran into her just as I was getting off my shift. We chatted for a second
and then she asked if I wanted to have a drink.

Over the next couple of months, we got together every time she was in
town. I had made a decision that I was going to try one more time to be
Jerry. So I stopped shaving my legs and I let all my body hair grow out. I
purged all my female clothes and vowed to quit dressing. I said goodbye to
Brooke and that was the end.

Mandy and I dated for almost a year and then she asked if I wanted to move
to her town and live with her. I had nothing holding me back so I agreed.
We became a couple and she was very understanding with my occasional
inability to get an erection. She said, ‘All men have a problem once in a
while.’ I found a job with a recruiting company and found I was quite good
at it. It was almost all over the phone I had a winning way with people.
Soon I was making as much as Mandy. I started to feel better about myself
and I finally took mom’s advice and started doing yoga myself. I started
to tone up and I lost a little weight even though I was still ‘thick-
thighed’. My flexibility increased exponentially and soon I was almost
good enough to teach the class instead of being the student.

I asked Mandy to marry me and she said she would and we had a big church
wedding. I remember standing at the front of the church with Zack as my
Best Man and seeing Mandy’s dad walk her down the aisle and thinking, ‘I
would so rock that wedding dress.’ I shook my head and wondered where that
came from. We went through with the ceremony and started our lives
together. Mandy was very career oriented and she was in the process of
climbing the career ladder. She got promoted a couple of times and then
started traveling.

One night while she was out, I was looking for a cuff link and so I
started searching drawers in our bedroom. I opened her underwear drawer
and the scent hit my nostrils. I was so overwhelmed that I sat on the bed.
I stared at the open drawer for what seemed like an hour. Then I stood and
walked over to it. I looked in and saw a beautiful peach colored camisole
and matching bra and panties. I touched her things and closed my eyes. I
was swept away in a wash of feminine thrills. I quickly stripped off my
clothes and put on her things. I looked in the mirror and for the first
time in two years saw Brooke staring back. I started looking through
Mandy’s closet. She was a size 8-10. Her bras were tight around my chest
but the panties fit like my own.

I sat around for a while and just tried to absorb what was happening. I
was married. We had a house. I couldn’t do this. I had to try to be a man.

Mandy had told me that she didn’t want k**s so I had a vasectomy. Then
after about the first year, our sex lives dissipated to almost nothing.
She was tired or working or traveling. I had a few friends from work but
it wasn’t like I was known all over the city. I tried to fight. I really
did. But over the next 6 months, Brooke started to live again. Living with
a woman who was also brunette and was almost the exact same size, didn’t
help my effort to be Jerry.

One Friday afternoon, when Mandy was spending the weekend with her
parents, I took the afternoon off. I was sitting there watching TV and
having a glass of wine. I was wearing that same peach cami and matching
bra and panty set along with a rose colored silk shortie robe. I couldn’t
take it anymore. I went down to the post office and got a PO Box. Then I
came home and got online. I ordered a shoulder length brunette wig with
banks and highlights. Mandy and I didn’t wear the same show size so I went
to Google and queried women’s shoes. Almost $800.00 later, I moved on to
make up and skin care. Next I moved to the trans sites where I found the
most realistic looking breast forms I could find. Mandy and I maintained
separate bank accounts so I wasn’t worried about being found out. By the
time I was finished that night I had spent almost $2,000.00. I also
downloaded a ‘female voice tutorial’ that I began practicing every spare
minute. I still had my foot locker even if it was empty and it was up in
the attic. Mandy came back to town for a week on the next Thursday and
then was going to be gone for almost 3 weeks on her next trip.

I put her on a plane on Wednesday evening. On the way home I stopped and
bought Nair. I got home and took off all my clothes and within 30 minutes,
I was totally bald from the eyebrows down. I put on a royal blue short
silk nightie and got a glass of wine. I sent an email to my boss and told
him I was sick and would out Thursday and probably Friday. I drank a
second glass of wine and then went to bed. I woke the next morning after
sl**ping better than I had slept in 3 years. I got a cup of coffee and a
silk robe and watched some television while I gave myself a pedicure. Soon
I had pretty red toenails and they looked very sexy as I stretched my
totally hairless legs. After they dried, I got up and put on a pair of red
lace panties and a pair of my wife’s jeans. It was one of the last warm
days of fall so I wore my own sneakers and a light brown t-shirt. I didn’t
care if anyone noticed the man with the hairless arms. I went to the mall
and window shopped getting ideas for things I could order online. I also
stopped at an earring shop and by the time I left, I had two gold studs in
my left ear and one in my right.

It was about noon so I went home and put on my wife’s bikini and grabbed a
glass of iced tea. We had a privacy fence around our back yard so I wasn’t
concerned with getting caught. I took a copy of glamour magazine and my
tea and sun tan lotion and lay in the warm fall sun for almost 3 hours. I
tried to give my longish nails the best manicure I could and painted them
the same color as my toes. I turned a couple of times and by 4:00 when I
came in, I had tan lines no boy should have. I made a salad and put on the
white lace cover up. I watched one of the talk shows and the news and then
went back to our bedroom. I hopped in the shower and shaved as close as I
could.

I sat in front of my wife’s vanity and started my makeup. First concealer
and then foundation was followed by powder. I decided that for effect I
would do my eyes a bit more dramatically than I usually did. I was going
to a bar that catered to trans people so I figured the light would be low.
Once finished I stripped naked. I then applied the adhesive and breast
forms to my chest. I had decided on a ‘B’ cup and I was really very
pleased with how they fit and looked. I applied a little makeup to the
edges and looked in the mirror. They looked and felt and moved so
realistically, I almost thought I might feel it when I pinched the nipple.

I selected a matching bra and panty set that was berry color. The panties
were bikini style and almost transparent. I had to relieve myself and then
tucked myself away. I then selected my wife’s apple colored silk cocktail
dress that came to about 4 inches above the knee. I had a terrible time
getting the back zipped but finally managed. I had decided to go without
hose as I had noticed many women doing. It felt so yummy with my naked,
hairless legs. I then put on the matching open toed sling back mules with
the 3 inch heels that I had ordered online. I took everything out of my
boy wallet and changed it over to my girl wallet and tossed it in my purse
with the rest of my necessities, (hair brush, lipstick, tissues, nail
file, tampon, KY jel, condom) I found a light blush colored lace shawl and
it was almost 8:00. It would take me 30 minutes to get to the bar so I
spritzed myself once with Nina Ricci and took one final look in the
mirror. I felt such excitement and peace and total joy.

I went out to my new Honda Accord and smoothed the back of my dress as I
sat and then turned my hips and brought both legs inside together. I put
my purse on the passenger seat and buckled my seat belt which accentuated
my breasts. I hit the garage door opener and started the car. It was an
uneventful trip other than I felt pretty again. I arrived in the same
neighborhood as the bar I was going to but found that I had to park almost
2 blocks away. I turned off the car and put the keys in my purse.

I checked my hair and makeup in the vanity mirror on the visor one last
time and then grabbed my purse and opened the door. I swung my legs out
together and stood. I closed the car door and hit the lock button and
began my walk to the bar. Hearing my heels as they clicked on the pavement
was so erotic along with the cooling fall air as my silk dress swirled
around my bare, hairless legs and panty clad bottom as it jiggled. I
neared the door and there was no cover charge. The bouncer looked at me
and smiled as I walked in the front door.

It was almost 8:45 and the place was starting to fill. I walked over to
the bar and sat and the bar tender said, ‘What’s the lady drinking?’ I
answered in my best girl voice, ‘I’ll have a cosmopolitan please?’ and I
smiled at him. He smiled back and I began to look around the bar and saw
lots of ‘obvious trans’ girls with heavy garish makeup and semi slutty
attire. Some that seemed to be a bit more on the scale towards TS. I was
sitting next to a girl and we started a conversation. Her name was Terri.
She commented about never seeing me before and how pretty I was. She
looked at my breasts and said, ‘Hormones?’, I shook my head ‘Breast forms.
You?’ She said she had been on hormones for a year. I was fascinated. She
was self medding and hadn’t gone full time yet. She worked in an office
and people were starting to ask questions. She had to wrap her boobs so
others wouldn’t see but it was uncomfortable and she was thinking about
talking to HR. She told me where she bought the hormones and I made a
mental note of the website.

I was about finished with my drink when the bar tender delivered another.
I looked at him and he said, ‘From the gentleman.’ and nodded to a man at
the end of the bar. I followed his look and saw a tall, (like 6’6′)
handsome gentleman with short blonde hair. He appeared to be about 40 tan
and fit. We made eye contact and he raised his glass and smiled. I smiled
back and raised my glass to him. It only took him about a minute to wade
through the now packed bar to my side where he introduced himself as Tom.
I stuck my hand out as femininely as I could and said, ‘Brooke’ and he
took my hand and kissed it, ‘Pretty name for a pretty lady.’

So we talked. I’m sure I went on like some sort of airhead but he was
polite and listened and also talked. He was a successful business man and
he wanted to know what I did. I told him I was a ‘headhunter’ and he made
a little joke which I giggled at and batted my eyes. He asked if I wanted
to dance and I said yes and we made our way to the dance floor. After
about 45 minutes we moved back to where I was sitting. He ordered another
Cosmo for me and a Scotch for himself. We chatted some more and finished
our drinks. I was tipsy again and feeling very sexy. He said he was in
town on business and had appointments in the morning. He looked me
straight in the eyes and said, ‘Let’s go back to my hotel for a nightcap.’
I nodded and I asked him where he was staying. He was at the hotel that I
had walked past on the way here from my car. I giggled a little and told
him that and he helped me with my shawl and off we went.

We left the bar and he offered his arm and we walked to the hotel. My
heels clicking and my panties covering my bottom and I was so turned on
that I would have let a one eyed homeless man fuck me. We took the
elevator up to his room and he unlocked the door. He helped me with my
shawl and I told him I wanted to freshen up a bit. I took my purse into
the bathroom where I touched up my makeup and re-applied lipstick. I also
took the KY and lubed my ass up as much as I could. When I finished I peed
and washed my hands and opened the door. He was standing there with two
glasses of wine and had turned the television on to a music channel that
was playing very softly in the back ground. I set down my purse and took
the glass of wine. We clinked glasses and took a drink.

I set my glass on the desk next to his and he leaned down and took my chin
in his fingers and he gently kissed me. I kissed him back and then he took
me in his arms and kissed me fully. I felt his tongue begin to probe and I
willingly opened my mouth to receive him. We kissed passionately as he
held me and I began to moan a little. I could feel his erection against my
tummy and I wanted his cock in me. He took a step forward and I took a
step back and felt his bed behind me. I sat down and reached up to
unbuckle his belt. I unzipped his fly and his pants fell to the floor. He
was wearing boxers and they were tented out with his hard cock. I pulled
down his boxers and his erection sprang into view. I looked up at him and
he looked down at me, ‘Suck my cock, bitch.’ he commanded. In no time, I
was sucking his dick and licking his balls and mewling like a kitten. Then
he grabbed my arm and said, ‘Turn around and get on your knees with your
ass in the air, slut!’ I did as I was told and he roughly pulled down my
panties and stepped in behind me. As he entered me, he wasn’t gentle. He
was bigger than anything I’d ever taken back there before and by the time
he pushed forward about 5 different times, I felt his tummy up against my
ass. Then he just started pounding into me. I could feel my ass and thighs
jiggling as he fucked me.

I don’t know if it was the alcohol or what but he went on for a good 15
minutes like that. I had moved a little so that each time he entered me he
hit my ‘spot’ and so I was very into it. I was moaning and saying ‘fuck me
hard daddy’ and ‘Give me that cum’. He was calling me names like ‘fag
slut’ and ‘cock whore’. I’m not sure why but I liked that. Finally he
said, ‘Ohhh you bitch…I’m gonna…..cum….’ and with that he gave me one last
massive thrust and we collapsed on the bed as he cummed in my ass. I also
had an orgasm as I felt his moistness in my bottom. We were both exhausted
and lay there for at least 5 minutes as his cock went soft in my ass and
began to feel him leaking out of me. Eventually, he rolled off of me and I
stood and went to the bathroom with my purse. I freshened my makeup and
tried to clean up but his cum was leaking from my stretched out ass.
Suddenly I remembered the tampon and I inserted it just like a girl on her
period.

I pulled up my panties and walked back out. He was asl**p and so I
gathered my things. As I picked up my shawl, I saw a note with some cash
next to it. The note said, ‘If a $100 isn’t enough whore, wake me.’ I
looked at the cash and counted out 5 $20 bills. I put the money in my girl
wallet and left. I loved the feeling of being a sexy girl and walking down
the street with my heels clicking on the pavement. I got to my car and hit
the key fob to open it. I opened the door, sat and swung my sexy legs in.
I drove home and took a shower with the breast forms still on. It was 2:00
am and so I put on a black lace nightie and went to bed.

It was almost 11:00 when I woke the next morning. I got up, took 2 Advil
and grabbed a cup of coffee. As I began to feel human, I realized I had to
pee. I went into the bathroom and then realized that I still had the
tampon in me. I pulled it out and then a large glob of cum leaked from me.
I finished and went back out to the living room. I took the red polish off
my nails and replaced it with clear polish. I put my wife’s bikini back on
and then some jeans, a sweat shirt and a coat to hide the breast forms. I
got my ID from my girl wallet and put it in my boy wallet. There was a
chill in the air and I headed out to a tanning salon. I purchased a
package of 18 sessions and then went back to the bed. I took off my
clothes and sneakers and climbed in. After about 20 minutes the timer went
off and I got dressed and went home. I took off my clothes and the bikini
and stood in front of the mirror. God, I loved having tan lines and boobs.
My ass was a little sore from the night before but about 6:00 I decided
that I wanted to go out again. I had a salad and then got in the shower
where I shaved. I was going to have to do something about that. I put on
my makeup and did my nails. Then after they were dry I found a pair
matching pair of cream colored panties and bra. I took my wife’s beige
sweater dress and put it on and then put on a pair of nude panty hose and
a pair of cream colored pumps with a 3 inch heel. I changed everything
over to my purse and I was out the door by 8:30 and at the bar by 9:15. It
was a Friday night crowd and a little more rowdy than the night before.

I ordered a glass of wine and I ran into Terri again and she wanted to
know everything about what happened the night before. I had pretty much
finished the story when a couple of guys approached us and asked us to
dance. We danced for like an hour and then back to our table. Eventually,
Terri left with her guy and I left with mine. I followed him back to his
apartment. He was gentler and it was very nice but I he still filled my
ass with cum and I had to use another tampon.

Saturday night I stayed home and played in the chat rooms. Sunday I took
off the breast forms. I had to use a special solvent and it took a couple
hours. Monday, I went in and talked to my boss. I asked him how he would
feel if I worked from home a couple days a week. I made up a story about
Mandy and I thinking about having k**s and since most of my work was done
on the phone anyway, he gave his okay. So that’s how my life was then for
about a year. Tanning salons, and pretty panties and letting guys fuck me.
Working from home on Fridays and Mondays and having my wife travel 1 to 3
weekends a month. I even had laser hair removal done on my face and chest.
Mandy and I weren’t having sex anymore and I had moved into the spare
bedroom.

Then I met Malcolm.

The End

For the most part, Mandy and I now had separate lives. When she traveled,
I was now almost living full time as Brooke. I was even going out during
the day to the grocery store and running regular errands as Brooke.

It had been over a year now and I had been through a lot. I had lost both
my parents in a car accident. It didn’t take long to close their estate
and when we sold the house and everything in it, I netted about $150,000.

I was sometimes getting confused and speaking in my Brooke voice when I
was Jerry. Work was fantastic. I was now working from home all the time
and only had to go in once a month for team meetings. At least 3 times a
week, I was going out with my new friends and being crazy. I had even let
a few guys take pics of me sucking cock or getting ‘spit roasted’ and then
they were getting posted on the internet. I was hanging out more with
Terri than I was with my wife. She was now living with a guy and looking
for a doc to get her through transition and ultimately surgery.

I put Mandy on the plane one Wednesday night and went home. I had a few
work things to do before Friday. I had my left ear pierced three times now
and my right one twice. The only time I wore studs was when Mandy was in
town or I had to go in for a team meeting. I had let my own hair grow and
it was down to the back of my neck. I had it styled in a feminine cut but
when I was in Jerry mode, I just pulled it back in a pony tail.

I had started self medding about 6 months ago. I could no longer wear
Mandy’s size 10 clothes as I was now a size 8. My measurements when I
started ‘mones were 40-31-34. After only 6 months, I was 37-29-36. I
almost couldn’t wear my Jerry clothes anymore because the tops were baggy
and the bottoms were tight. When I went in for team meetings at work I had
to really ‘butch up’ but I still got looks from people. I had boobs. They
weren’t an ‘A’ cup yet but they jiggled when I walked and if I wore a t-
shirt or went topless, it was pretty obvious. I had done my homework and
discovered that male to female trans, could expect breast growth to be
about one cup size smaller than their mom’s. Mom was a ‘C’ cup so I
figured I would end up around a ‘B’ cup.

Thursday I got all my work done early and had a nice dinner of a salad and
fruit. I put on a pretty yellow nightie with my now always red painted
toes and got a good night’s sl**p. I woke the next morning at 5:00 am and
got showered and dressed. Terri was there by 6 and she drove me to the
doctor’s office for surgery. About a month ago, I had started seeing
Terri’s gender ther****t and my meds were now ‘legal’. We got to the
clinic around 6:30 and I got checked in. No food. No Liquid. Check. I was
given one of those hospital gowns with the open back. About 7:30 the
surgeon came in and checked my chart. They had me sign some forms saying
I was cool with what was about to happen. He took my hand and told me not
to worry. Then he left and the nurse gave me a shot. About 2-3 minutes
later I was like high as fuck. At about 8:00 they came in to take me down
to surgery. Terri kissed me on the cheek and went to the waiting room.

They wheeled me into the operating room and there were a couple of nurses
and the doctor waiting for me. They moved me to from the gurney to the
table which had stirrups like a gynecological exam table. They nurse
hooked me up to an IV and told me to relax. The shot was in full effect by
now. The doctor sat on a rolling stool and slid between my legs. He lifted
the sheet and then, ‘You might feel a little sting or a pinch.’ He was
right but then after about 10 minutes. Everything was completely numb.
Then he said, ‘Scalpel.’ He leaned in and did something which lasted about
10 minutes. ‘f***eps’ and then about 10 minutes later the nurse handed him
stainless steel dish which he put something in. ‘Sutures’ he said. The
nurse put the dish on the tray and I looked over. I saw 2 lumps of tissue
about the size of a walnut. The Doctor stood up and said, ‘We’re done
Brooke.’ My orchiectomy was over. My testicles were gone. I didn’t have to
take Spirolatone anymore and I was committed. It was my 27th birthday.

After I came around they gave me a couple of bags of ice and Terri drove
me home. She spent that Friday night and helped me with ice bags and such.
By noon the next day I was still taking Advil and ice but able to manage
for myself. By Monday I was able to work since I worked from home. By the
following Friday I was pretty much up and around. I went in to have my
sutures removed. After the doc was done he gave me a mirror. I was stunned
how much smoother I was. I pulled up my panties and tucked what was left
of my boy parts back and I was even more amazed at how flat I looked.

I stayed home that weekend but by the following weekend, I was ready to
party. It was Saturday May 15th. It was warm outside (like 80 degrees) and
Mandy was with her parents for the weekend. I had bought some denim shorts
online that were so short I had to wear thong panties with them because my
ass cheeks almost showed. I also wore a white ‘wife beater’ tee and no
bra. I wasn’t even an ‘A’ cup yet but my nipples stuck out and I looked
like a slutty school girl. I also work a pair of white wedgies with a 2
inch cork sole. I styled my hair after I got out of the shower and I was
just amazed at how I looked ‘down there’. If I didn’t tell you, you would
have bet I had a vagina.

I did my makeup and my nails and when they dried I grabbed my purse and
headed out. I got to the bar around 9:30 and all my friends were glad to
see me. We did a couple of tequila shots and I was feeling it when a 3rd
shot arrived at our table. I looked at the server who simply said, ‘From
the gentleman’ and nodded over to the corner. I looked up to see a bald
black man with a diamond stud in his left ear. He smiled and raised his
glass. I smiled back, tossed back the shot and then let the glass linger
by my lips. He stood up and my eyes almost fell out of my head. He was at
least 6’9’and buff. He walked over to our table and stuck out his hand,
‘I’m Malcolm’. I took his hand which was at least 3 times bigger than mine
and said, ‘Brooke. Would you like to join us?’ He smiled and sat down.
Malcolm was a former NFL player. He had gotten hurt and now ran his own
gym. He was charming and funny and sweet. We drank and danced together and
all my girlfriends were jealous. When we slow danced together I could feel
his cock. It felt like it was as big as my forearm. About 1:00. He leaned
in and whispered in my ear, ‘Let’s get outta here, baby’.

I nodded and we left. We walked to my car and I gave him the keys. For
some reason, I decided to take him home. I had only done that a few times.
Most of the time, I went home with a guy, it was their place. We got home
and pulled in the garage. Got out and walked in the kitchen. I no sooner
set down my purse that he had his arms around me in a deep passionate
French kiss. He picked me up and carried me into the living room to the
sofa. He pulled off my top exposing my little boobs and then leaned down
and sucked on them. That sent me through the roof and I moaned very
loudly. He sucked one and then the other. The one he wasn’t sucking, he
played with and tweaked it between his fingers. I lay back on the sofa
with my head lolling back and moaning. The he lifted up my butt and pulled
off my shorts and my thong panties. When he saw my little cock without her
partners, he smiled and then he went down on me. I was in heaven.

Then he stood up and unzipped his pants and let them fall to the floor. I
was right. He was almost as big as my forearm. We proceeded to a very hot
69 while he kept putting his fingers in my ass and then using more saliva
until he was banging my ass with 4 fingers all the way up to his hand. I
got up and staggered out to my purse and grabbed the KY and came back in
and lubed up that hard black cock as best I could. The he stood and picked
me up again. He bent me over the couch and stood behind me. I could feel
him at the entrance to my ass pussy. He pushed forward a little and I felt
a pop as the head entered me and then I saw stars. He stayed still for a
minute and then moved forward again. Again it hurt like crazy. He took it
out and put some more KY on his cock. Then he stepped forward and I felt
him at the entrance to my ass pussy again. He pushed a little and I felt a
pop as he the head entered me but it didn’t hurt as bad. Then he pushed a
little more and I took it little by little until after 5 minutes I felt
his stomach touch my ass.

Slowly we fucked. Building a rhythym with each other. He told me how
‘tight my pussy is’ and how he was ‘gonna be fucking my pretty white ass
all the time.’ He asked me how much I ‘Liked nigga dick’ and I just
moaned. He told me to beg for it. ‘Call me Daddy tell me you love black
cock.’ ‘Yes Daddy, I love black cock’ Tell me you ‘just a white fag ‘ho
who needs big black cocks 3 times a day. ‘Yes Daddy, I’m just a white fag
‘ho that needs big black cocks 3 times a day.’

He reached up and grabbed my hair and pulled my head back, ‘Ya bitch, ride
that black dick’ He was pounding into me now. ‘Gonna cum bitch. Gonna fill
that white fag ass!’ and he plowed forward as he pushed my head roughly
down on the sofa. I screamed,’Yes Daddy, Fill my hot white fag ass with
your cum!’ He tensed and then started shaking and I felt the familiar
moistness in my ass pussy as it filled with cum. Then he collapsed on top
of me and I lay there in his massive arms with his softening cock inside
me.

All of a sudden, I heard a familiar female voice say, ‘What the fuck is
this?’ I opened my eyes and it was Mandy standing there in her robe with a
look of disgust on her face. Malcolm stood up and his cock pulled out and
left me gaping with cum running out of me. Mandy just stood there and said
to him, ‘You better leave.’ I stood up with just my shoes. My makeup was a
mess and my little tits were so very obvious with the larger areola and
the hard girl nipples. My waist had begun to narrow and my big butt was
now bigger and my thick thighs were now thicker. You couldn’t see that my
nuts were gone but my dick was smaller than it had been because of all the
estrogen. Cum was running down my leg.

Malcolm got dressed. ‘I ain’t got no ride’ and Mandy coldly said, ‘Wait
out front, I’ll call you a cab.’ I looked at Mandy who just sneered at me.
‘Well. The little fag likes black cock huh?’ I was totally embarrassed and
said nothing. ‘Go fucking put some clothes on bitch.’ She went into the
kitchen and opened the fridge and grabbed a beer.

I slipped past her and went back in the bedroom and put on a short robe
with some of my girl slippers. I inserted a tampon and pulled on a pair of
plain white panties and then went back out to the living room. I sat
across from her with my legs crossed while she drank her beer and laughed.
‘Fuck…I married a panty boy.’ I asked if she had called a cab for Malcolm
and she said she had.

‘When did you get home?’ I asked her. ‘I got in about 10:00 tonight. I
thought I would surprise you so I took a cab. You weren’t home and I was
tired so I went to bed. Then I was awakened by some little fag with a
giant black cock in his ass screaming ‘fuck me daddy’ so I got up.’ she
sneered. I was silent and then after she finished her beer I said, ‘I
assume you’ll want a divorce. I’m going to fully transition to female.’
She turned and said, ‘How long have you been on hormones?’ I told her
close to seven months. She looked at me and said, ‘Well at least I didn’t
lose you to another woman. Yes I want a divorce and I can’t afford for
this to be messy so we’ll have to do it quickly. You already look like a
girl. God you’re even pretty.’

With that, we each went to our separate bedrooms. My sl**p was fitful and
when I woke the next morning I was a wreck. I went pee and took out the
tampon and the biggest glob of cum ever fell out of my ass pussy. I hopped
in the shower and tried to freshen up as best I could. I went out for
coffee with no makeup and Mandy was already sitting there. She glanced up
and shook her head. ‘I want you out of here as soon as possible. In fact,
I’ll pay for the hotel until you find a place if you’ll just go now.’ So I
packed up my laptop and my mobile phone and went in to grab my clothes. I
made another decision then as well. I left all Jerry’s clothes behind and
only took my clothes. I drove to the hotel and Mandy followed me in her
car. We went in together and she gave them her card.

I went up to the room and called Terri and told her everything. We agreed
to meet at the bar that night. I lay down and took a nap and when I woke
it was almost 7:00. I quickly did my makeup and put on a cute denim mini
with a pastel yellow tank top. I went braless again but wore some very
sheer pastel yellow panties with lace around the legs and a flower in
front. I didn’t feel fancy so I just put a pair of flat sandals, grabbed
my purse and out the door I went.

When I got there, everyone was all there. I walked in and sat down, I
ordered a glass of wine and waited for Terri. I just sat there thinking
when I felt a presence next to me. I looked up and it was Malcolm. He gave
me a sheepish smile and then said. ‘Listen, I think you’re really hot and
would like to get to know you better. Will you have dinner with me?’

I smiled and nodded. I sent a text to Terri that something had come up and
Malcolm and I headed out for dinner. This time, he followed me back to the
motel where I left my car. I hopped in next to him and we went to little
out-of-the way Italian place with red checkered table clothes. Malcolm had
the veal and I had lasagna. We talked and laughed for what seemed like
hours and we shared a nice bottle of red wine. I invited him back to the
hotel and we made love for what seemed like hours. All I know is I woke up
next to him the next morning and I was sl**ping in the wet spot. I also
checked my bottom and I was still gaping a little. That made me hot all
over again that I was enough of a woman to take on a ‘monster’ cock like
that.

We spent the day together on Sunday and made love again before he left
that night. He had to be up early and I had things to do as well. I got up
the next morning and showered. I did my hair and makeup and called the
office. I asked my boss to meet for lunch on Wednesday. That was the last
time I used the Jerry voice. My next call was to a prominent divorce
lawyer in the city and I made an appointment to meet with him Tuesday
afternoon. Then I called a well known salon and made an appointment for
that afternoon. I wanted a cut and color, mani/pedi, eyebrow threading…the
works.

I had a few hours and so I made a few business cold calls as Brooke and it
seemed to go very well. In fact, I got fewer questions about why I was
calling a male executive than I did as Jerry. Go figure. Anyways, I put on
a matching lilac colored bra and panty set under a mauve and white polka
dot sun dress with a halter and open back. I put on some white pumps with
no stockings and headed out to my salon appointment. Four hours later, I
walked out of there with a cut very similar to Jennifer Aniston and my
hair was now ash blonde. My eyebrows were thin and femininely arched and
my perfectly manicured fingers and toes had a very pretty hot pink polish.

I stopped at the mall and promptly dropped another $1,000.00 on a couple
new outfits that I thought Malcolm would like taking off of me. I headed
back to hotel just in time to meet him and we went to dinner and a movie.
Then he took me by his gym and introduced me to everyone their as his
woman. Then he took me back to the hotel where he filled my tight little
pussy with his cum again. This time was more like the first with lots of
dirty talk and a little rough. The next day I went to the tanning salon
early and then met my divorce lawyer that afternoon. He needed a $1,000.00
deposit and so I wrote him a check. He told me to let him handle
everything and considering my situation he didn’t see a problem.

I met Malcolm for dinner and he was charming as usual. This time we went
back to his ‘crib’ where he proceeded to fuck my brains out 3 times before
taking me back to the hotel with my tampon in place. I slept in the next
day and then got up and got ready to meet my boss. I selected a navy blue
matching push up bra and panty set and navy blue thigh high stockings. I
took the tags off my new navy blue skirt suit and then put on a crème
colored blouse that showed just a little cleavage created by my push up
bra. My navy blue 3 inch pumps along with two small gold hoops, two pearl
studs and a diamond stud completed my ensemble. I drove to the restaurant
where I was meeting my boss and walked in. Several heads turned as I
walked in. I finally found him at his table and walked over to him. ‘Hello
Eric,’ I said as I sat down. He looked up and said, ‘Sorry Miss, I’m
meeting a …’ and his words just stopped as he recognized me.

He stared and I finally said, ‘Eric honey, stop staring and order me a
Cosmo.’ He shook his head and asked for an explanation. I told him some of
the story that I thought was important then I asked him point blank if he
would be okay if I bought out my non compete for $20,000.00. He asked me
what I was calling the new firm and I told him Brooke Benson and
Associates. He agreed and we finished lunch. I told him I simply had to
dash and I felt him looking at my butt as I left the table so I put a
little extra wiggle in my walk.

The lawyers took care of the divorce in about a month. She kept what she
had coming in to the marriage, I kept what I had. We split all the joint
property and I kept my inheritance. After about 6 months, the divorce was
final. I had already formed my corporation and was working as Brooke
Benson. I met with an attorney who was recommended by my transition shrink
and he did the paperwork to change my name to Brooke Bethanie Benson.

After a year, of living full time as Brooke, my doctor gave me all the
necessary clearances to have my SRS surgery. I am now a full ‘B’ cup. My
dress size is almost a perfect 6 except occasionally my ass is too big for
a 6. I’m engaged to Malcolm who tells me that black men like big butts so
I shouldn’t sweat it.