Note: This story was dynamically reformatted for online reading convenience.
 
 

   WARNING!

   This story is of sexually explicit material if you are not of legal age
or do not wish to stop now otherwise enjoy.

   Feedback is always appreciated.

   Darien567@aol.com

   Josie



   It started out as every other Friday night.  I was going to my favorite
bar for some something to drink, dance and maybe some pussy.  Well it
didn't quite work out that way.  I went in and said hello to my friends and
looked over the crowd.  Most of the girls were the same that were there. 
There were a couple of new faces though.  One in particular caught my eye.
She was about 5' 6 inches maybe a 32 cup.  She was slender nice legs and
tight ass.  She had long red hair and a black mini-skirt and a fur coat.



   A couple of guys had danced with her but she kinda brushed them off
afterwards.  I asked Sheila the waitress what she was drinking.  She told
me had a bloody Mary.  I had Sheila take her another one.  She pointed me
out and I sat there for a few moments.  Then I saw the bulge and the skin
and I walked over to her.  I leaned over and whispered.  "I think you need
to go to the ladies room because it's coming out of the pouch." She looked
at me shocked "oh God." "Don't worry I'll hold the table for you." "Thank
you." She hurried to the ladies room about fifteen minutes later she came
back.



   I ordered fresh drinks for her I was drinking rum and coke.  She came
back "thank you I'm so embarrassed." She started to get her purse and coat.

   "Where are you going?

   "Stay I'd love to have some company with a beautiful woman such as
yourself." She looked at me "it doesn't bother you that I'm." "Transgender
no, it doesn't bother me in the least." "I'm bi-sexual and into most
anything." "So no it doesn't bother me now put down that purse and let's
dance." She put her coat and purse down." I motioned for Sheila and she
came over "can you check her fur coat in for me.

   Sheila smiled as I told her to start a tab.

   I took her hand and we went to the dance floor.  A slow dance came on
and I pulled to me.  I was holding her my hands caressed her tight ass.  I
could feel as she got hard.  We danced three dances and had to take a
break. I found out her name was Brandy.  I told her my name was Daniel. 
Sheila had come back with the claim check and fresh drinks.  She asked
where I worked I told her that I didn't work anymore.  I explained that
both of my parents were killed in a car accident with a drunk driver.  She
told me she was sorry.

   "I guess it was fate for I was supposed to be with them and had to work
late." "The driver was working for a trucking company." "He was falling
down drunk and my parents said were killed on impact." "The driver survived
and went to jail.  I sued the company and settled out of court." "In other
words you're well off?  "Is that why everyone likes you?  "Probably some of
them but all of them know if they need help then I'll help them if I can."

   She looked at me "I don't know too many people that'll do that." "Drink
up we don't want to talk about gloomy things we want to enjoy ourselves."
"After a couple more drinks and dances she started to open up." "I work for
a temp agency doing customer service work for different companies.  I
laughed "I'll bet they love you." "Most people won't do that kind of work
because people get arrogant and rude with them."

   I could tell she had a nice buzz going and I asked if she was hungry. 
"Sure" she said and I called for the bill.  I paid for it and dropped a
fifty as a tip.  Sheila smiled and thanked me.  She brought Brandy's coat
to me.  I helped her put it on and we walked out.  I asked if she drove or
took a cab.  She told me she rode the bus.  I hailed a cab and had him take
us to the Red Lobster down the street.  We went in and I treated her like a
real lady.  We had lobster and shrimp and wine.

   She told me she hadn't been treated this way in years.  We had been
there for over an hour and were thoroughly enjoying ourselves.  We sat
talking and eating.  I asked if she had to work the weekend.  She told me
that she didn't work weekends.  We finished and I paid the bill and we went
to my place.  It was in a secluded area of town that was totally private. I
had a large pool and Jacuzzi out back.  I took her hand and led her to the
Jacuzzi.  It was large enough for six people.  She was to say the least
surprised for I had a very large home.  I went to her and started slowly
kissing her.  My hands were slowly caressing every inch of her.

   I unbuttoned her blouse and tossed it aside and started kissing and
licking her nipples and they were real.  I told her to take her high heels
off.  She did this while I kicked my shoes off and pulled my socks off and
I took my shirt off.  She started to unbutton her min-skirt and I stopped
her.  "Let me" and I went back to running my hands over her.  My hands were
caressing her tight ass.  "I can't take anymore stop teasing me." I
unzipped her mini and pulled it off.  I started kissing her deep and long.
My hand was rubbing that cock of hers through her pouch.

   She let out a groan and I relented and took her cock out.  "Take your
garter and hose off." She couldn't get them off fast enough.  She had a
small cock but it was rock hard and practically begging for relief.  "Do
you want to cum?  I whispered.  She moaned as I pushed her back.  I ran my
tongue from her balls to the head of her cock.  She was begging and I
simply slid her cock all the way in my mouth.  I was sucking her as hard
and slow as vacuum cleaner.

   She moaned then groaned and I felt her balls tighten.  She gasped as I
held my mouth there with her entire cock in it.  "Oh God I'm cumming and
she was bucking against me holding my head on her.  I was sucking every
drop and she started to go limp.  I started sucking her hard my head
bobbing up and down her cock.  She was as hard as a rock once again.  I
pulled her cock out of my and she was startled.  "Please don't leave me
like this." I licked the cap of her cock.  I took and slid my hand down her
cum soaked cock.  I rubbed one of my fingers around her "pussy." I then
slid the tip of my finger in her pussy.  I took and literally suckled the
head of her cock.  She let out a groan and moaned.  Brandy tried to shove
her pussy down on my finger but I had other ideas.

   Once more she shot her hot seed into my mouth.  Her body started to go
limp I whispered in her ear "parties just starting baby." I slid her in the
Jacuzzi and turned it on high.  The water was warm and the jets pulverized
both of us.  I started kissing her she tasted her salty cum in my mouth.  I
turned her over the edge and slid my cock around her pussy.

   "Ready for some man meat she was like an animal in heat." I slowly
gently slid my cock in her.  I didn't stop but rather slowly, gently buried
it in her.  I felt my balls as they slapped against her ass.  I let her get
used to it then I slowly started pulling it out and pushing it back in.  I
started with a slow steady motion then I picked up the speed.  I was
throwing her against the side of the Jacuzzi.  She was shoving back on my
cock grunting and groaning.  "Oh God please don't stop I'm cumming...  "Oh,
oh, oh fuck me hard!  "Ram it in me!  "Fuck, oh please don't ever stop.

   I shot a long hot stream of cum in her I didn't bury it in her.  I kept
fucking her milking my cock of all my cream.  I was finally limp.  She was
worn out but very happy.  I pulled my limp cock out of her she turned
around and started kissing me.  "I've never been fucked so good as you just
did." "That was just round one baby we have all night." I climbed out and
told her I'd be right back.  I came back with a bottle of champagne and two
glasses.  I opened it and poured both of us a glass.  I climbed back in.  I
handed her a glass and we took a sip.  I pulled her to me and we enjoyed
the Jacuzzi and the champagne.

   I kissed her again and again I pulled back "do you mind if I ask a
personal question?  "Go ahead." "Did you always want to be a girl?  "I had
no choice in the matter." "My mom and older brother cooked up the idea."
"They thought it would be funny making me a sissy." "So ever since I was
eight they started making me wear dresses." "My mom is a plastic surgeon
and they started making me take pills." "These enhanced the growth of
breasts and hips while losing weight in all the right areas."

   "My mom used plastic surgery on my face." "She did this to make me look
like a girl." "I had brown hair but she changed it to red and stopped
cutting it."

   "Mom was the only woman that I ever fucked my cock was bigger then."
"They got some kind of pills, hormones I think that stopped male growth."
"After mom had finished the surgery on me and I started growing breasts."
"My older brother Jonathon claimed that if mom got my cock then he would
have to break my "cherry pussy." "I was ten then and he had a big dick and
trust me it hurt a lot but he didn't care." "Mom has a friend that works in
the government." "Between them they changed my social security number and
birth record to female."

   "Now according to law I am a female named Brandy not a young boy named
Brian." "Where is your older brother?  "He lives in the next town over he
comes to "visit" at times."

   "You mean he comes to fuck you?

   "Does he have many friends?  "Not really and the ones he does have are
real creeps and perverts." "What would happen if they found him in a dress
with make-up.?  "Or being fucked by a guy and a transgender?  She looked at
me and laughed.

   "They'd make him a sissy to them for life."

   "Maybe we should give him an introduction."

   Two weeks later he came by her place for a "piece of tail" as he put it.
I had people standing by waiting for him.  Brandy told me when he came
over. We drugged him with a date rape pills.  We also gave him something to
be more "obedient." We took him back to his place.  My friends started in
on him they first bathed him, shaved his legs.  Then they put a life like
wig on him.  They then started putting make-up on him.  We dressed him in a
short clingy dress with false glued on breasts.  Sprayed him liberally with
perfume and had him sign a paper.

   Some of the girls called his friends to come over for a party.  They
never passed on free booze.  When I saw them coming down the road we
started fucking him.  They rang the doorbell and we told them to come in.
They walked in and saw him sucking Brandy while I had his dress pushed up.
They saw me pounding his ass.  Another one of the girls was sucking his
cock.  One of the girls told them to join in.  They were shocked as they
saw Brandy's cum running out of his mouth.

   "What the hell are you faggots doing to our friend?  Cum was running
from his ass down his leg.

   "We're an escort service and he rented our services." "He's a steady
customer so we give him a discount." "Steady customer you mean he's done
this before?  "What's your name?  "Mike, you say he's done this before? 
"He's been a customer for three years now." "We even sold him his breasts."
Mike walked in front of him.

   "You know all of us have needed pussy and couldn't get any."

   "Here you are not just getting it but putting out for it." "You also
liked this and you didn't think of us?  "Well the days of hiding things are
over." Mike dropped his pants.  Jonathon was on his hands and knees.  Mike
looked at us "what's his name?  "His real name is Jonathon but he like
Josie." "You mean Josie and The Pussy Cats?  "Yes that's why he likes that
name." "He also likes being taped." "Arnold get the video recorder Henry
and I'll get "Josie here" ready for her performance."

   He looked at us "I'm glad you called us, thanks."

   "We don't know any of you he gave us the number and had us call you."
"You mean he's wanted to party with us like this?  "Why yes he has wanted
to for some time but was afraid." "I looked at him he's talked about you
Mike he likes you." Arnold started setting up the camera and Henry had
brought some Vaseline out.  Mike looked at him "Josie have I got news for
you." "You have three boyfriends so you'll be real busy from now on."
"We're going to put you on the net and make a fortune off of you."

   "Ah Mike we've already paid for a video of him." "Don't worry we'll make
this first video for you." Brandy spoke up "if you plan on doing it right
here's a website." "There's a store nearby that'll help with the clothes."
"Last but not least here is a name of a "special bar" he likes."

   A month later Jonathon/Josie showed up on Brandy's doorstep.  He was
wearing a skirt and blouse.  "Brandy you've got to help me my friends are
turning me into a sissy." "But how can I help Josie you are one." "You
dress like one you have breasts like one." "Hell they probably give you
pills and you fuck all of them." "Do you do this Josie?  He looked at her
"how do you know they call me that?  She looked at him "because when you
called out you said it was Josie." "That's a sissy's name like "a pussy"
I'll bet they all fuck you." "Please Brandy let me spend the night,
please." "Okay but my boyfriend is coming over soon." She opened the door
and let her brother in.  She went in the kitchen and called me.  I came
right over.

   I knocked on the door and Brandy answered it "he's in here." I walked in
the other room "hi you must be Josie you sure are cute." "My name is
Jonathon not Josie." I walked over to him "you used to be but now you're
Josie." "Do your friends make you suck their cocks?  He held his head in
shame "yes, then why don't you show us how to do it." Brandy dropped her
shorts.  "C'mon big brother I need some to and I want you to suck me and
get me off." "I can't do that Brandy." "But you can and have been doing it
and I'm mad that you didn't save it for me first." "Take your panties off I
said." He pulled them off and dropped them beside her.  Brandy held her
cock at his mouth.  "Suck it" and he tentatively licked her cock.  I took
hold of his rock hard cock and egged him on.  "Keep going lick her balls."
"Take all her cock in your mouth you're a sissy." "You like it and know you
do or your cock wouldn't be hard." I was slowly jacking him.  "Take all of
her and taste her hot salty cum in your mouth." He had her entire cock in
his mouth.  He was sucking her down as she was shooting her hot cum in his
mouth.  I had stopped jacking him off and he was begging for it.  I looked
at him "get Brandy hard and she'll fuck you." "You can suck me off." I
looked at him "if I think you're not getting me or my girl off I'll fuck
dry." I looked him in the eye "trust me you will scream." I pushed my cock
to his mouth.  He hesitantly went to touch it.  "What's this shit you want
it but don't want to give it?  "No wonder your friends treat that way." I
went behind him and took the belt off my jeans.  He was confused "what are
you?

   My belt came down hard on his ass.  There was an angry red welt and I
slowly beat him.  Brandy was laughing "trust me you'll love it" she kept
laughing.  I stopped beating him and went around the front.  "Ready or
shall I start again?  He immediately reached for and had my cock in his
mouth.  Brandy had already sunk her cock in his ass.  As she shoved into
him I slid out.  We fucked him for days until he was a beaten man or shall
we say woman.

   Their mom had a cam on her computer.  Brandy sent her an e-mail to be
on-line at seven pm for a surprise.  Her mom was on-line and we brought
"Josie" out.  We had gone through his lines and what he was to do our get
beaten.  "Hi mom it's Jonathon or was I'm Josie now let me show you."
Brandy stepped up and Josie pulled her cock out and sucked her until she
was dry.

   I walked in back of him and we had put a lot of Vaseline in him.  I ran
my cock around his ass and then sunk it slowly in him.  She was shocked
here was her boy doing this he was sucking her off.  But he was thrusting
his ass on that boys cock like he'd been doing it for some time.  We both
finished with her watching she was angry and we could see it.  "Brandy you
know where I live.

   You bring "Josie" here right now and I'll show him what a true sissy is
and how she acts."

   "What about my friends they need me?

   "It's true mom he has three friends that fuck him daily." "You get him
over here this instant I'll train him." "As a matter of fact give them my
address and tell them to come over for some private parties." Brandy took
him over to her and we told his friends.  Brandy moved in with me and we've
never stopped fucking.  We've quit dating other people and I think I'll ask
if she'll marry me I know she will.  As for Josie their mom has started her
own private escort service.