From alt.sex.stories.tg Sat Dec 21 00:45:05 1996
Path: nienor.IN-Berlin.DE!forwiss.uni-passau.de!suelmann
~From: suelmann@forwiss.uni-passau.de (Michael Suelmann)
~Newsgroups: alt.sex.stories.tg
~Subject: TG: My Friend Jake
~Date: 20 Dec 1996 22:20:27 GMT
Organization: The Testsite
~Lines: 1121
Message-ID: <59f3fb$gd5@nienor.in-berlin.de>
NNTP-Posting-Host: elros.forwiss.uni-passau.de

I didn't write this nor do I know how to contact the author

TG, cd, mm						§§§§§§§§
Oroiginal Filenames: JAKE1.TXT .. JAKE4.TXT


                        MY FRIEND JAKE
                              BY
                           JO BLACK

What can I tell you about my friend Jake? I've known him for
20 years; we even went to grade school together. He's, to put
it mildly, a bit eccentric. To be completely honest, he's
crazy. That's probably why I like him. Whatever we do, it's
fun. For years, he has planned what he terms adventures for us to embark
uponm. They are always odd but extremely intresting. This is the story of our
latest one.

Naturally, since we've grown up, we don't see much of each
other. Once a month or so the last several years has been the
extent of our contact. He called last night and asked me over
to watch Monday Night Football. I eagerly accepted. Not just
because the Bears were playing, but because I have always had
a fascination for Jake and his antics. I know that football
will not be the only, and maybe not even the primary
entertainment of the evening.

Well, I got there an hour before kickoff as he had suggested.
After catching Jake up on my life, I asked him what he has
been up to lately. Mistake # 1. He told me and I listened.
Mistake #2.

Jake told me how he went to a bar called the Queen Mary in LA
during his last business trip. He proceeded to tell me how
all the waitresses, the entertainers and even the hat check
girl were really men dressed as women. For some reason, this
entire thing really intrigued Jake.

Now, by this time, you have to realize we had two pretty
stiff drinks and were working on the third. This really
released any inhibitions I may have had. Or perhaps, I should
say, this released any good common sense I may have had. We
talked about our senior play at good old St Simon High. Being
an all boys school taught by nuns, we didn't really have any
girls for our production of Romeo and Juliet. Consequently,
we drew straws for the lead parts and I lost. Yes, I was
Juliet to Jake's Romeo. And just why did we do Romeo and
Juliet in an all boys school? I told you, we had nuns. Jake
and I were always in trouble with the nuns, so we were
assigned the roles. I have no doubt that the nun's rigged the draw.

I thought back to the costume I wore in that play. Funny, it
wasn't all that unpleasant. The director, Sister Mary Paul,
insisted that Juliet was to be properly attired, 100%. I
always believed that she was just getting back at me. But
flashes of rustling silk on my thighs kind of sent a shiver
down my spine. I really liked the way the long haired wig
would dance on my face as I moved my head. Hey, don't get me
wrong. This was my only foray into crossdressing. But it was
pleasurable in an odd way.

A couple more drinks and the Bears were forgotten. Jake, as
usual, decided that we should do something different. Now,
Mistake # 3, and the biggest one, I said, and I quote, "OK,
I'm game."

Jake said that he discovered a small bar here in town that was very discrete
and VERY friendly. It was, quite naturally, a drag bar. Not only was the
entertainment and the employees in drag, but most of the patrons were too. He
decided that we were to go and to go dressed. Tonight.

I protested in many ways. I said we didn't have the clothes. He responded that
his sister had left her belongings with him. I groaned. Sally was a big girl,
not heavy, just big. I was sure her clothes would fit.

I explained that we didn't look like girls. He countered that we only had to
look like men dressed as girls. I tried my final plea. "But, I don't want to."

Jake just looked at me sadly and was quiet for what seemed several minutes.
Finally, he asked, "Why? You always do what ever we thought of before. But,
It's alright if you really don't want to."

Maybe it was the booze, maybe it was Jake's sense of betrayal. Or just maybe
my curiosity was also piqued. I don't know. But I agreed. Jake just smiled and
told me to come with him.

We went to his spare bedroom. He had two complete sets of clothes laid out on
the bed, complete with bra, panties, hose and shoes. He beamed and asked me if
I preferred the off the shoulder forest green or the red minidress.

I was almost totally flabbergasted by this point and told him I didn't care;
that he could choose. Another error. I got the red mini. And man, was it
short.  But I had given my word so I just smiled.

Jake then got down to business. He directed me to the bathroom and explained
that I needed to take a hot bath in bath oil and shave my chest and my legs in
order to be authentic. Strange to admit, I saw his point. That was one thing
we always did throughout the years when we would pursue our little adventures.
We always tried to be real.

As I soaked in the tub, I went to work on the shaving part. It wasn't easy at
first, but was easier than holding a razor to my next neck the morning after a
real binge. The chest was easier. A few swipes and I was done. I got out of
the tub and toweled off. As I dried off my newly smoothed legs, I found myself
lingering as I gently rubbed them and to my astonishment, I got hard.  Go
figure.

Jake replaced me in the bathroom, leaving me to fend for myself among the
alien undergarments on the bed. He told me he wouldn't be long, as he had
shaved the night before. So, he had planned this all along.

True to his word, he was out in record time. He asked me why I wasn't dressed
yet; I just shrugged, took a deep breath and pulled the bright red panties up
my smooth legs and tickled my half hardened cock as I pulled them into place.
I then picked up the matching bra, wrapped it around me and hooked in while it
was on backwards. Then, I pulled it around and pulled my arms through the
straps. Filling the empty cups with foam that Jake had provided, I felt a
little restricted after pulling on the pantyhose. But it was a secure type
restriction, not unlike being hugged. Glancing in the mirror, I was shocked to
notice the body before me. Oh, oh, that embarrassing lump in front had to go.
I pulled the hardened cock between my legs, but that just made it worse as it
looked like I was growing a third leg. Jake just laughed.

He pulled himself together and produced two leather pouch type things he
called gaffs. He claims ALL the "girls" wore them. I took mine and for the
life of me, I couldn't figure it out. Jake watched and laughed and snickered.
Finally, as tears ran down his face, he took the gaff, gently grabbed my cock
and fixed me up. I didn't even breath. When he grabbed me, I could feel myself
stiffen up. But it was odd, it felt damned good. Jake just grinned as he did
it. I know he held me longer than needed. But I didn't object. This was
getting stranger by the minute. But what was stranger, I didn't care. In fact,
I think I liked it.

We just stood there for a few seconds. Then together, we turned back to the
business of getting dressed. Jake had laid out the most silky black slip I had
ever seen. As I pulled it over my head and down the length of my body, I
shuddered with delight. I thought back to that play in high school and fondly
relived that feeling of silk dancing across my thighs. I just couldn't stand
it. I ran to the bathroom, pulled down my panties and the gaff and let my wad
go.  After regaining some control, I cleaned myself off, got rearranged and
quietly reentered the bedroom. Jake was sitting on the bed, silently watching
me. I sat down next to him. After a few minutes he gently took my hand and
said, " That happened to me the first time too. Nothing to be embarrassed
about, it happens."

I just stared at the floor for a few minutes and then looked up at him. I
knew. After all these years, I knew something I should have known. I
asked," How long have you been gay?"

"All my adult life, though I really haven't been too active until 3 years
ago."

I then asked, "This bar you want to go to tonight; is it a regular hangout for
you?"

He admitted that since it had opened 4 months ago, he had gone at least twice
a week. Like Cheers, everyone knew his name.

I shook my head with a smile. He got me. He kept his secret for years. He set
me up to go there with him. That was obvious. But I had noticed that he still
had his jeans on. I was his "date". He was dressed to go out. But why me? I
never had spoken of any desire to either dress as a woman nor gave any
interest in the gay lifestyle. So I had to ask him, "Why me?"

He started slowly, " You have always been my best friend, my partner in crime.
This was the only thing I never shared with you. I thought if I made the
situation so exaggerated that it was one of our adventures, I could explain to
you later about who and what I had become."

There it was. The man who had done everything to everyone just in the name of
fun was scared to go it alone. I felt that old sense of obligation again. I
stood up, stared down at him with my hands an my hips, my breasts jutting out
and said, "Just don't sit there. I need help with my dress before I can put on
my makeup. And you need to change too. If you're taking me out, you better
plan to wear good slacks and a sports coat. And one more thing, buddy. You're
buying."

As I smile passed my yet plain lips, Jake stood up and hugged me! He just held
on for a moment and whispered, " I knew you would understand. I know this
isn't your scene and that you are doing this just for me. Thank you." And
then, all of the sudden, the old Jake was back in control of himself and of
our planned adventure.

I picked up the red minidress gingerly with both hands. The fabric was cool
and soft to my touch. I stepped into it and slowly slid it up my legs, the
fabric sliding up my slip. I felt myself get hard already! Am I doing this for
Jake of for myself? I was a little confused. This was a first for me. I was
really enjoying the entire experience. I pulled my arms in the sleeves and
adjusted my simulated breasts. I turned and with a surprisingly soft voice
cooed, " Jake, could you please zip me up."

I could feel his rough hands fumble with the end of the zipper. He grabbed the
tongue of the zipper with one hand and my ass with the other. Just for
leverage, I'm sure. But I almost exploded inside. The firm grab just felt
right. As the zipper slowly slid up my now satiny back, I again felt those
shivers running through me. I hoped it would never end. But alas, It did. I
turn on one foot and faced him. He just stared back and muttered something
about how incrediblably different I looked. I was pleased.

I slid my feet into the 3" red heels that Jake had left on the floor. Perfect
fit. That in itself wasn't that surprising. We both wore the same size and
knew it from gym class years ago. I walked tentatively around the room. I was
pleased to discover that I had no problems with balance. I just needed to
shorten my natural stride. I'll say one thing, high heeled shoes are the most
feminizing part of female apparel. My all even rolled slightly as I walked. My
hips swung slowly with each step. I glanced into the mirror was pleased.  And
that in itself was a surprise. I no longer felt self conscious or nervous.
Hell. I didn't even consider I was dressing like a woman, I felt I was one.

I slid slowly over to the vanity. Jake had laid out enough makeup on the top
to paint the Radio City Rockettes. I found the makeup was the easiest of all
these peculiar preparations. In high school, we had to learn to do our own
makeup for the play. I applied the foundation expertly, covering the heavy
jawline. Then I worked with the blush and powder to highlight my cheeks. The
eyeshadow was too much, but I felt like showing off. The eyebrow pencil worked
perfectly after a quick plucking. I added lip liner and lipstick as red as my
dress. The final touch was sable brown mascara which seemed to double my
eyelashes.  I looked in the mirror and suddenly panicked. My hair! What about
my short, conservative hair?

I held Jake bustling about behind me them felt something come over my head. I
looked in the mirror and there it was. Cocked to one side, but beautiful just
the same was a great mass of curly brunette hair. " Remember, Juliet? I do.
The way you tossed your head and the hair would play across your face?" Jake
had remembered all these years. I wondered if he suspected what joy I got from
being Juliet. I might ask him later.

After fussing a few minutes, my hair was perfect. I glared judgementally in
the mirror. Hair, makeup, everything looked just right. I rose slowly, and to
my great surprise, quite gracefully. I pivoted on the toe of one high heeled
foot and faced Jake. He had changed into tan Dockers and a sports jacket; just
as I had asked. Suddenly, a wave of cold went through my body. I whispered, "
What now, Jake?"

"Now, my darling Joe, without an 'e', we go to Fantasy Island. No, not the
show, the place I was telling you about."

I almost had an anxiety attack. It was enough to submit to Jake's plans. I
agreed to getting dressed and going with him. But the mere thought of actually
going out in public never really hit me. But, what the Hell, I've gone this
far, let's do it and get it over with. I know at least no one will be there
that I know.

He magically produced a pure white cape from God knows where and swept it
gallantly over my shoulders. I fluttered down my arms and back and I felt
myself stir once again. Damn, I've got to get that under control or this could
be a longer night than I feared. But I just smiled and turned to Jake and
said, "Let's go."

He directed me through the kitchen by gently grabbing my arm and leading me.
That was nice. I felt cared for in some way. In his large, attached garage, He
gallantly opened the passenger door to the little Mustang. After a moment of
indecision, I remembered how my dates entered cars and slowly sank my lovely,
silky ass into the seat. I then, not ungracefully, swung my legs in and folded
them at the ankles almost demurely. Oh well, it worked.

Jake opened the garage door, started the engine and turned to me and said,
"Jo, you'll enjoy this evening. I promise. If I go too fast or try to do
something you don't want to, tell me. We've been friends too long to screw it
up now. We are going out just like always, as friends. What ever you want to
do when we arrive, just do it."

I couldn't respond to any of this. Jake was my friend. I really didn't feel
any electricity between us as I had with any girl I had dated. And I didn't
feel any strong passion toward me. I honestly think that we are still just
friends. Although I am now wearing a slip and a minidress, this felt just like
one of our old adventures. We were out for a good time.

The trip to Fantasy Island, Jake said, was 20 minutes. During that time, we
made small talk. A few times he grabbed my arm or hand, but he didn't linger.
I was his friend, I decided. In fact, I was probably accorded the same status
as a sister rather than a date. He mentioned a few things about letting him
know if things got a bit intense or if I was feeling uncomfortable with
someone, he would rescue me.  Now I knew I wouldn't have to ask him about the
play and if he knew how much I enjoyed my role.  He evidently sensed what I
either didn't realize or refused to recognize those many years ago. I was
totally enamored at dressing as a woman.  He was doing this as much for me as
for him!  Jake always did know me best.

The club turned out to be at a little strip mall. He pulled around the back.
Fantasy Island had a large parking lot that was ringed by one of those 8' high
privacy fences. In addition, there was a security guard at the gate. Jake
rolled down the window, said a few words and was waved through.

The lot was packed. I estimated over 100 cars were parked in the rows. Jake
pulled the car into a vacant space in the back of the lot and killed the
engine. He always parked in the back of any lot to protect his doors from
dings.  He got out of the car. Funny, I sat there, waiting, no expecting, him
to come around and open the door for me. Which, of course he did. After all,
if I went this far, I was going to be treated as a lady.

This time, he interlaced his arm in mine and gently led me across the lot. I
could hear the heels tap in rhythm as we approached the door. I could feel the
cool night air run up my dress, which was about 4 inches above my knee. The
cool wind flicked at cock and caressed my thighs. God, there are advantages to
this. It sure felt good!

When we reached the door, he paid the cover charge and led me to the coat
check. There, behind the counter was one of the most beautiful creatures I had
ever seen. More than 6 foot tall, bright blue eyes, she was wearing the
traditional costume; the flame red, sequined bustier, black seamed stockings
and hells that were 4 or 5 inches high. But what I found remarkable was her
poise. She was outgoing, even  a little flirtatious. But she was acting like a
real woman, not a man acting like a woman. I remember the rehearsals for the
play and the direction that I was given. Sister made me repeat actions over
and over again, until they became natural. These included walking, sitting,
talking and even the slight turn of my head that caused my hair to swirl. I
got it. If I was here, dressed like this, I would be the same kind of woman as
the coat check girl. After all, if it smells like a bear, if it looks like a
bear and acts like a bear, it must be a bear.

******************************************************************************
 This ends Chapter 1. The next Chapter will deal with the bar and my
experiences there. Tune in!

                  Love,
                     Jo


Jake  Part 2
  In which your author completely loses control of the
situation and learns a lot about him/herself.
*************************************************************
    As the door leading to the bar opened, I was amazed. I
could hear a blues band in the background playing softly. The
lights were bright, but not harsh. I guess I had judged this
place by Jake's personality. I had expected a frenzy of
flashing lights, accompanied by the loud, harsh beat of
Metallica. I considered this a good sign. I felt out of place
in modern clubs when I wear jeans and a sportscoat; in my red
minidress, I certainly was self conscious enough.
     Jake again gently wrapped his arm into mine and lead me
toward a table right in the middle of the barroom. And this
room was huge! There must have been over 100 tables scattered
throughout the room. At the head of all this, was the most
ornate, mammoth oak bar I had ever seen. And believe me, I've
seen a lot of bars in my day. There were at least 40 stools
around this wooden Goliath, almost all occupied. The entire middle of the vast
room was a polished wooden dance floor. My eyes had not yet adjusted to the
light, so I couldn't really see who was who (as if I'd know, anyway). Jake,
suspiciously being the perfect gentleman, pulled out my chair and I,
surprisingly, glided very gracefully into it, again demurely
crossing my ankles. I had to cock my legs to one side because
of the heels. Looking down, I noticed how elegant and almost
flirtatious this looked. My legs, now long and smooth,
assumed an unnatural (for me) shapeliness because of the
heels. My silky hose almost made them gleam. I felt a faint
stirring in my crotch. Oh no! Not now. At least I could wait
until I get a little bit acclimated. No dice. I turned myself
on!
     Here's the picture. I'm perched upon a chair, looking
like some middle-aged siren on the make in the middle of a
gay bar. There are at least 150-200 people here, who I
presume are all Gay, and with my luck, on the make. I never
planned to come here, I really don't believe I am here,
dressed like this. I am very uncomfortable and embarrassed.
And THIS is the time I choose to get a hard-on?
     I realize that Jake is asking me something. I smile
nervously and ask him to repeat it. "Scotch ok?", he had
asked.
     I told him ok, but make it a light one. I thought I
would need my wits about me before the night was over.
Besides, Jake had laid out a bustier which certainly reduce
my waist and given me a more girlish figure. But it was hard
to breathe at times and I'm sure it would put pressure on the
bladder. That was a scene I didn't want to think of yet.
     I glanced at the waitress and almost collapsed.  I
instantly could tell that this was a guy, about my age.
He/she was dressed in a low cut black, satiny cocktail
waitress uniform.  It was complete with starchy petticoats
which made a SWISH as he made any move.  Perched on his head
was a very realistic wig (I guess). It was blonde and fell to
his shoulders. His makeup was very much overstated; almost
whorish. On his feet were the highest heels I had ever seen.
Jake gave him our order and he slunk away with his petticoats
swishing behind him.  Now here's an interesting moment. I
checked him out from head to foot with a critical eye. Not
because of why he was wearing such an outfit, but I was
judging his taste on how he was dressed. I recall thinking he
was rather slutty!  This was a real shock.  I could feel
myself falling further and further into my role.

     Our drinks came rather quickly. Our waitress smiled and flirted with
Jake. She slammed my drink down in front of me. Surely, she didn't consider me
competition? Jake attempted to make small talk but I didn't know what to say.
As we fell silent, I looked around the room.  Most tables had a couple at
them.  Most of these couples were two men.  But in the corner, I spied a
couple of tables with women at them.  Considering my environs, they were
probably like me. No, they planned to come here. I wonder what they were like.
Jake muttered something about going to see a friend. I panicked again.  "No,
don't leave me alone!", I pleaded.
     "It will just be for a few minutes", he said. "Remember what we talked
about. We are here only as friends. I need to circulate so the others realize
that. Besides, I think that they others also need to realize that you are
available." He quickly added with a sparkle in his eye, "If that's what you
decide you would like.  I told you, no pressure. Do what you feel like. But,"
he added cryptically, "give it a chance. I remember that play and I know you
do too.  For one night, relive it. Explore it further. You may enjoy it. If
you don't, at least you'll know that too."
     He left a twenty on the table to cover any drinks I would want. I sat
there, too scared to look around any further. This entire scene was getting
more and more complex. I was used to the clothes by this time. In fact,
whenever I moved, I could feel the stiffening in my groin. The underwear, the
hair and the makeup was becoming a positive feature. I slowly lifted my head
and glanced around the bar again. This time, I noticed more detail. Men were
laughing and holding each other. This didn't seem that out of place to me for
some reason.
     I sipped at my drink and continued to look around. I heard the now
familiar tap of heels on the wood floor. I looked over my shoulder and spied a
redheaded vision. She was about 5'8", a little shorter than I. Her emerald
green dress slid suggestively off her left shoulder. I noticed with some
astonishment that her hosiery and 4" heels matched the outfit to a tee. I
nodded politely, not knowing what to say to a beautiful woman when I was
dressed like one. I heard in a soft, but slightly deep voice, "May I join
you?"  I just grinned like a fool and nodded again.
     She slid into the chair exactly like I did. For some reason, this pleased
me. She set down her suede purse on the table and unclasped it, took out a
cigarette. Wordlessly, she offered me one, which I took. Silently, she slid
two out of the pack, pulled out a gold lighter and lit them both. Not really
remarkable, unless you figure I quit smoking 5 years ago.
     The waitress came by and she whispered, "Vodka gimlet and freshen up my
girlfriend's drink at the same time. I heard the swish, swish, swish of the
petticoats heading toward the bar. I gazed at my new companion. She smiled and
after our drinks came and the swish disappeared into the dark, she finally
broke the ice. "First time I take it."
     "Why would you say that?", I wittingly demanded.
     "Because you act exactly like I did 3 months ago when I made my debut",
the redhead sang. "Look, I was even more nervous than you are. I had only
dressed in private. I learned makeup from magazines. I saw you with Jake when
you came in. He told us last week that he had a special friend he was going to
bring in tonight. Just asked us to be friendly."
     I was more confused than before. Not only had Jake planned this entire
evening, he was so confident in the outcome, he told everyone except me. I
felt my cheeks redden. I'm sure my eyes reflected my ire because the redhead
shook her head and said, "Hey, don't be upset. I only came over because I know
the first time is almost impossible. You are in an alien environment with
completely foreign clothing on and have no idea how you feel about it. I was
the same way. Jake told me that you had repressed these feeling for many
years; but other than that, I understand exactly what you are going through.
This can be fun. However, let's make a little deal. Try it. At least you know
that way if this life is for you. I won't stay with you all night because I
don't want to cramp your style." (I don't know how to refer to people at this
point. From now on, the person's gender will be reflective of their dress.)
With a leer, she licked her slips slowly and purred, "I don't want to miss any
opportunity myself. Jake helped me that first night. He gave me advice and
offered suggestions throughout the night when I needed them. I owe him that so
I'm going to help you"
     She said her name was Renee. She started with hints on female deportment.
I was poised just perfect to her discerning eye. But I was leaning back into
the chair. She showed me that sitting straight caused my breasts to highlight
my dress. I was pleased. As Renee continued, I honestly grew more interested.
She demonstrated how to hold a cigarette and even how to gently puff at it,
not take long drags, like a man. When I wasn't using my hands, I learned how
to tuck them properly on my lap. She even commented on my walk as I had
entered the bar. I learned a lot. Looking at the clock, I was shocked to
discover that more than an hour had passed. Renee noticed this and said that
there was only one more thing to learn. She instructed me to get the money off
the table and grab my purse and follow her. I rose, just as Renee has told me
to. I did just fine until I discovered that my right leg had fallen asleep.
Shaking a bit, I was able to revive it and suggestively shaking my hips
slightly from side to side, I followed Renee to the exit.
     The restroom! I hadn't considered that. I grabbed her arm and said, " I
can't go in there" She just laughed and maneuvered me into the sacred door
that proclaimed, "LADIES". I was mortified.
     When inside, Renee almost cried, she laughed so hard. Between sobs, she
asked, "Just who do you think uses the Ladies room in a gay bar? Come, let's
get busy."
     I finally found out why it takes women so long in the restroom. Undoing
this and that, pulling up slips and dresses etc. It was even worse when I was
finished. It seemed that everything had slid up. My breasts were now 6"
higher, my dress was 4" shorter and my hose were 4" lower. I worked at it for
what seemed quite a while, until it felt right. Exiting the stall, I glanced
into the mirror and confirmed I was back in shape. In fact, as I lingered in
the looking glass, I was very pleased with what I saw. The Scotch had really
brighten my cheeks. My hair was a little disarrayed, which was rather
pleasing. My legs just seemed to go on for ever. What was the old saying, O
yea, "...all the way up to my ass". I got out my makeup while waiting for
Renee. I puttered a bit, not out of necessity rather just to reflect. I was
here, I have decided I was pretty. And quite frankly, I was feeling more
aroused the longer I was here. But now what. I needed to decide.  I either was
going to go back out and sit at the table like a lump, find Jake and whine
that I wanted to go home. Or, and I don't believe I am even considering this,
I could, well, try to make some, well, new friends. That's all. I have
decided. I would go back out and participate. Just enough to get a feel for
the lifestyle. Besides, I never heard of a gay man wanting a woman. I was
dressed as a woman, so therefore, I was the safest man here. What a fool I
was. But I knew it at the time. But it was a good release valve. Renee said
she was ready. I stood up, still facing the mirror, applied more lipstick in
an almost defiant manner. I then clasped my purse with a snap and turned on my
heel and headed out to face my destiny.
     Renee and I parted. She promised she would be "around" until closing. I
stood in the entrance and looked around the room. I didn't see Jake anywhere.
I noticed the other girls were still in the corner. But I didn't feel like
being with " the Girls". In the restroom, I had resolved to see this little
charade all the way through. I figure I'd go to the bar, order a drink and let
nature take it's course. The bartender was the most gorgeous creature I had
ever seen. At least 6'3", with arms and a chest developed like a body builder
without getting that beachbum type look. His black hair was in tight curls
which perfectly framed his face. Deep blue eyes finished off this vision of
Grecian virility. The sudden acknowledgment of these feelings surprised me but
I wasn't really embarrassed by them. I don't know why, but it seemed OK to
admire him. I didn't WANT him, but was attracted to his masculinity.
     I perched myself on the high stool. I crossed my legs a little awkwardly
at first. But with the gaffe I was wearing, my balls didn't inhibit this
movement. I sat there with my drink when someone sat down next to me. I stole
a glance out of the corner of my eye.  My new neighbor was just an ordinary
guy, a lot like I was a scant 3 or 4 hours ago. He had brown hair, jeans and a
rather ordinary blazer on. He cleared his throat and stammered, " Could, could
I get you, you know, another drink?"
     I felt an alarm go off in my head. This was it. I was being hit upon. I
was at the point of no return. Either run toward the exit or .."No thank you,
I just ordered this one. But thanks just the same. I smiled at him friendly
like, no in retrospect, it must have been almost eagerly.
     He smiled and asked if I would like to join him at a table. I agreed
instantly. I was committed. I was with a man and not just a little excited by
it! Sam briefly muttered something to the bartender and then turned to me and
rather cavalierly swung his arm and turned his palm upward.
     He followed me as I looked for a table. The place had really filled up
but I spied one, again, almost in the middle. When we arrived, he almost
tripped trying to get to the chair before me in order to hold it out. I
approved. By God, I've evidently decided when I dress like this, I will be
treated properly. This caused another blush to my cheeks. I was no longer a
man in a dress, I was a true crossdresser. So be it.
     He introduced himself as Sam. I said my name was Jo. He told me how
pretty I was. I blushed. I told him how handsome he was. He beamed. This inane
conversation went on for 5 minutes until and old favorite of mine, "Michelle"
came softly cascading across the sound system. I perked up a little. Sam
looked puzzled and then I could see the light bulb go on over his head. "Would
you care to dance, Jo?" I said I would be  delighted.
     He lead me toward the dance floor. There were a few other couples out
there, but no one dressed like me. He took my right hand in his and pulled his
left arm around my reduced waist. He had the lightest touch I had ever felt! I
awkwardly turned and stepped to the music. When the Beatles were finished, Sam
released me and we parted slightly. With a puzzled but somewhat endearing
little boy grin, he said, " That was nice. But next time, could I lead?"
     I was mortified. Here I was feeling that I had caught on pretty well, and
now I had reverted to my old masculine ways. Overconfidence will get you
everytime. I blushed, of course. That is ONE thing feminine I had picked up
rather well. Then, the entire bar seem to fall quiet for a second. From
somewhere, a disembodied voice announced, "Now for your dancing pleasure, our
manager and owner has requested a special song. He said it is dedicated to a
beautiful lady."
     The time honored strains of "Unchained Melody" filled the room. I had
always loved this song. Sam pulled me toward him. This time, however, he
firmly grasped me around the waist and pulled me tight. You remember how we
danced at the Senior Prom; both arms around your girl, holding her firm. I
felt secure for the very first time that evening. I surrendered myself to his
lead. I felt myself go a little limp. To support myself, I draped both arms
around his neck and clasped my hands loosely. After the first stanza, I was
almost ready to swoon. Feeling lightheaded, I laid my head on his shoulder.
There. The deed was done. I had crossed (no pun intended) from man to real
woman. I felt protected. I felt wanted. I felt pretty and desirable. And most
importantly, I felt the rock hard cock in my beautiful panties. God, was Jake
ever right! This was one of the most touching moments of my life. The song
seemed to go forever. I was a million miles away in the arms of a man who
desired me!
     After about a hundred years, the song slowly died away. I finally
realized that we were still clinging to each other in the middle of the dance
floor and no music was playing. Sam must have gotten the same idea because we
let go. I deliberately held firm for a moment. I wanted Sam to know how I felt
without any verbal explanation. When I released him and moved back a step, I
could see in his eyes that I communicated my emotion very well.
     He reached across my back and grabbed my shoulder. Hugging me tightly, he
directed me back to our table. He ordered another round of drinks. We didn't
say anything; we just stared at each other. I was almost oblivious to anything
around me. From my mind's eye, I saw someone nearing the table. It was
accompanied by the now familiar swish. swish of the waitress' petticoats. I
glanced away and saw the whorish one who had first waited on Jake and I went
we arrived. I returned my attention to Sam when I heard a crash.
     I jumped but too late. The little bitch and dropped my drink and spilt
it. I suddenly felt the cold liquid running down my dress and onto my legs.
Looking down, It looked like I had wet myself. I started crying!
     Sam was up in a shot. He grabbed the towel from the whore and started to
wipe my dress. His face was reddened, I noticed. He was embarrassed! Wrong. He
turned to the waitress and said, "Bobbi, you're through. Get out."Bobbi had a
little smile on her face as she dropped the serving tray on the table. She
spat,"Serves the little bitch right. Who does she think she is, anyway?"
     Sam grabbed my arm and said, "Don't cry. Come with me. We'll get you
cleaned up"
     I was in a daze. What was he talking about?
******************************************************************************
 OK, Ladies. This was part 2. I might have gotten a little long, but it's my
story. Stay tuned for part 3, coming to a BB near you soon. I welcome all
remarks, private or public, good or bad. Just drop me a line?

                                            Jo Black


                         Jake Part 3
                              by
                           Jo Black

In which I come to grips with some rather hard subjects.
(Yes, it's a joke)
************************************************************

     Sam led me back toward the bar. I followed defeatedly.
After what I had gone through this evening; just coming here,
and confronting my feminine side which was hidden from even myself. And
then, accepting the situation, and now all that is gone. I am
just humiliated. My red mini, in which I discovered who I was
and what I wanted, was ruined. And worse of all, I was the
focal point of attention and curiosity from all in
attendance. As we approached the bar, I saw Jake balancing
from leg to leg nervously. When we got that far, he looked at
me almost fatherly and said, " I'm so sorry Jo. I didn't mean
for this to happen. I wanted this to be your night. Come,
I'll take you home."
     As I started to nod, Sam cut in. "No, it's alright,
Jake. It was my girl who caused all this. I'll be damned if
I'll let it completely ruin Jo's big night. If that's OK with
you, I mean, Jo."
     Part of me just wanted to say screw it and leave this
dream and return to my past reality. But some perverse side
of me said I'll stay with Sam for a while. Unfortunely, this
perverse side also controlled my power of speech! I guess I
really wanted to stay. Jake gave me one of those shiteatin'
grins of his and said, "Good for you! I'll be around."
     Sam then directed me to a door by the end of the bar
which declared, "Employees Only". He guided me down a short
hallway to a door marked "Manager" and produced a key ring
from his pocket and unlocked the door. I heard him snap on
the lights and he bade me to enter. Yes, I'm sure that I was
the last to realize that Sam was the manager. No wonder that
waitress was pissed off; she was jealous of me, little old
me. Go figure.
              Jake closed the door behind us. He handed me a dry towel and
said, "now you just wait here. I'll go see what I can scare up." He left but
returned rather quickly. In his arms was an old white fluffy robe! " Here", he
offered, " just go into the bathroom and slip out of that wet dress and put
this on. Then, after you've had time to compose yourself, we'll see about
putting you back together."
              I gratefully took the robe and headed into his private bathroom.
I slid out of the dress and after a quick inventory, also discarded my slip.
The drink had started to dry and I was rather sticky. Spying the adjoining
shower, I decided what the hell and undressed and slid into it. I was very
careful to keep the water off my face and hair. Stepping out of what was the
quickest shower I had ever taken, I then patted my now rather smooth and silky
body dry. I noticed some Shower to Shower powder and doused myself liberally
with it. I then put on the bustier and panties. Everything else was unfit. I
sighed, put my foot into my heels, and opened the door. Sam was seated at his
desk. On this desk was a steaming porcelain teapot with matching cups and
saucers. He glanced up and smiled. "I thought that tea might help you relax. I
know it always helps me."
              What a sweet gesture! Only, I have never cared for tea much but
the idea seemed just perfect. I slid into the chair across from the desk. I
took my tea and it was perfect. I immediately felt better. Sam started to tell
me how he had acquired this bar and all. "I had been a loan officer for 8
years at the bank. In this capacity, I was expected to follow up on our
clients. I came in here one noon. It was very quiet and empty. The owner, whom
I had made the loan gave me coffee and showed me the books. It was phenomenal!
In the 2 years in which the bar had operated, he had earned enough to pay off
the loan."
              " We talked for quite a while that day. He was tired of the
business and wanted to retire to Florida with his wife. With my knowledge of
the loan history and having seen the books, I asked him flatly what he wanted
for the place, lock, stock and barrel. He told me, I gasped, and said, OK,
it's a deal. I went down to the bank, got a loan and that was that."
              "It wasn't until that night that I discovered that the clientele
was rather specialized", he laughed. "But there were no other problems with
security or anything, so I held onto it. And I've done well. The only change I
have made was updating the decor and putting the security fence in the back.
It's all increased business."
              He paused a few moments. Then slowly, he continued, "I never
thought myself gay of bi or anything. I dated a few women but nothing I really
found memorable. Naturally, being in this business, I investigated it some,
but never thought I could proceed. Until tonight. When I saw you at the bar,
with the light behind you, I was grabbed by a giant fist. I just thought you
were perfect. When I was dancing with you, I knew this could be it. You're as
beautiful as any woman, but are not. You are as vulnerable as any woman, but
are not.  What you are is yourself. Even now, sitting there in that old robe,
you are definitively female. Not just the way you look, but the way you're
sitting, the way you are acting. So, if I'm attracted to you, I still don't
know if I am Gay, Bi or straight. All I know is I want you. Let's sort the
rest of this out later."
              I was stunned. He wanted me. I wasn't shocked about being with a
man. No. I was stunned because he wanted me as much as I wanted him! I
stammered through my most current blush, " But.but. . are you sure you want
ME?"
              He laughed. "Oh, yes, my dear Jo. I've wanted you ever sense you
laid your head in my shoulder while dancing."
              Bingo! That's as long as I've wanted him! But damn, I've never
done this before; what do I do? Literally, I have never envisioned how to
sexually please a man. OK, it never came up when my parents told me about the
birds and the bees. And I don't think now is the time to call dear ol' Dad for
the second lesson. I started to shake nervously.
              Sam must have noticed because he refilled my tea and his hand
lingered across mine. He slowly comforted me. "Hey, I know. I've never done
this before either. My customers have given me, in great graphic detail I
might add, what they prefer. But, I would prefer we were spontaneous. Do what
ever feels good."
              I smiled broadly. "That sounds perfect. But I'm such a mess. For
our first time, I want it to be just right."
              Same said, "Honey, just remember where you are. Let's run down
the hall to the dressing rooms and you can pick out just what you'd like."
              Now that I had decided to "do it", my mind shifted gears. "No,"
I demanded, " If I am going to please a man, the first step is dressing to his
tastes, not mine. YOU go down the hall and find whatever you think is the
sexiest outfit there and bring it to me. While you're gone, I'll redo my
makeup and get ready."
              Sam explained that the door at the back of his office was also
his living quarters. He asked if would prefer to dress there. He had a vanity,
he said, and a small bath off that. I thought that really felt more intimate.
Imagine, I'll ready myself for my man in the boudoir. He would wait
impatiently as I primp and make sure everything is perfect. Then I would make
my grand entrance. I quickly agreed.
              The living quarters were neat and very masculine. All the
furniture was heavy, dark wood. The was a leather couch and matching recliner
in the corner. I spied the door to the bedroom, took a breath and entered. I
just stood there for a moment. The decor was identical to the antechamber.
Heavy, dark woods, but it seemed very comfortable and strangely homey. I
looked around for a bit and then sat on the edge of the bed. And I mean the
very edge. Here I was at the scene of the crime. I would surrender my
virginity here on this bed! I am going to be deflowered! I realized that all
these phrases from Danielle Steele seemed very trite. But, whatever gets you
through the night.
              I heard a knock on the door. Sam had returned. "Are you decent?"
he had asked. No, you idiot, I'm preparing to get screwed by a man! "Yes,
please come in."
              Once in, he deposited the most beautiful nightgown I had ever
seen on the bed. It was minty green with delicate little lace around the hem.
I picked it up and felt it's silky texture. It was like heaven. The front
wasn't cut terribly deep. Rather, it had flows of the green cascading down the
front. The back, however, was severely cut to the waist. The right side had a
long slit up it. It was gorgeous. He had brought matching pumps with what had
to be 5" heels. There was an overnight case also. Sam explained that one of
his "girls" had packed everything I would need. I shooed Sam out of the room.
"I'll call you when I'm ready; not before."
              After Sam left, I opened the overnight case. I guess Sam's
"girl" did pack all the essentials. I started to layout the contents on the
vanity. I found several different types of lipstick, mascara, powder and the
such. I found one packet which contained fake fingernails. Now there's
something I've never had. The stockings were the most sheer I had ever seen or
touched. They had a tint of green in them. I just pulled them slowly across my
face and felt my cock stir again. There were panties, the same shade of green
and as sheer as the stockings in the bottom of the case. The matching bra was
strapless, with cleverly placed wires in the soft curves of the cups. She had
even enclosed what I determined could only be fake breasts. They were firm but
had some give to them. In the front, there were even nipples in the
appropriate places. The last item in this Pandora's box was a bottle of
"Passion" with a note wrapped around it. Pulling the note off, I read:

                   You lucky Doll. Most of us have wanted to be the
                   first with Sam. I saw you when you came in. You
                   are just right; pretty but also real. Remember,
                   Sam's a real nice guy. Don't hurt him in any way.
                   But good luck and enjoy.

                                 Cindy

              The evening keeps getting curiousier and curiousier. This is the
second "girl" that I know envies me. Well, this must be worth pursuing. I
turned my attention first to the makeup. I corrected my slightly disheveled
face. I added some longer fake eyelashes that I found into the case. I then
turned to the task of the fake nails. I read the directions which seemed clear
enough. And, for the first hand, they were. Have you ever attempted to pick
off those little backing sheets with the fake nail. I persevered and finished
them up. I held my hand out and was amazed how they appeared to slenderize.
The long, red nails seemed to flicker like lighting bolts out of my
fingertips. They were energizing. I felt a surge of power throughout body. I
was excited that I could feel such strength from such a feminine thing.
              I then turned by attention to the underlayments. The panties
felt almost like a whisper as caressed by thighs as I pulled them up my legs.
I then adjusted the gaff and all semblance of my gender were gone. The bra was
trickier. I finally snapped it in front and spun it 180 degrees into place. To
my delight, I found the falsies filled the cups perfectly. I looked in the
mirror and was shocked. I was close enough so I could see only my body in the
looking glass. The supple curves blended perfectly with the gossamer like
panties. I slowly slid my long tipped fingers down the sides of mt panties. I
could feel the straining in my gaff. I stopped and took a deep breath. I
needed to wait.
              I slid the garter in place and started the long journey from my
toes to my thighs. As I brought the stockings up the leg, I could feel the
touch of butterflies, flitting at my now engorged crotch. I grabbed the towel
I had laid on the vanity and quickly pulled the minty panties down, undid the
gaff and felt the warm, milky liquid pump into my towel covered hand. It
seemed I would come all night. Finally, the pressure had relieved itself. I
just sat there, feeling a calm running over me. It was drained my physical
tension but I felt an emotional tension that was even stronger. I just wanted
Sam more now.
              I got up and quickly cleaned myself off and repowdered my upper
thighs, cock and balls.  After rearranging myself, I slid into the green
heels.  I had never felt so vulnerable as I did with those shoes on. I could
only take short, mincing steps. I felt that my newly acquired breasts were
pulling over in front. I continued to pace across the room toward the bathroom
and back to the vanity until I felt some type of grace; or at least some type
of balance.  It was time for the crowning touch, the gown.
              I found that my hands were shaking now with anticipation. I
slowly raised the gown toward me and just clutched to my chest. It was so soft
and so incredibly silky. I raised it over my head and let it, ever so slowly,
slither down my now soft, feminine body. It felt the lace at the hem as it
tickled my nose and cheeks. As it made it's descent, I swear I could feel it
hardened my nipples as it passed. Then it flowed across my flat stomach.  And
then, it made contact with my panties and stockings. I was hugged by the silk.
It had completely encased my body. I realized that I hadn't breathed at all as
it fell across by skin.
              I glanced in the mirror and was delighted. There was someone
else here now. My former self was gone. Now, only Jo remained. The vision in
the mirror could only be female. The gown had covered me like melted plastic.
It took the exact same line as the body underneath. When I breathed, I could
feel it expand and contract, rise and fall, just like my it wasn't there. It
was almost like a second skin. But this skin was silky and shimmery in the
lights. I posed in the mirror. I put one foot in front of the other, tilted my
chin up a bit, cocked my head to one side with my one hand on my hip, the
other on my thigh. God, I was gorgeous! This one moment was worth all the
hassle tonight. I smiled rather wickedly. I then applied a redder shade of
lipstick, very heavily. My lips glistened as though they were wet from the
rain. Well, the time had come. My lips would be wet, but not from the rain.
              I spun on the ball of my right foot and floated to the door. I
was now complete. This body in this gown was unmistakably in charge. (Helen
Reddy should be so proud). I slowly opened the door and let in sort of creak
open. I waited until it stopped on its own accord and then confidently strode
into the next room and struck my pose. "Sam, I'm ready now."
              Poor Sam was thunderstruck! He just sat in the recliner in
obvious shock. He just stared. Then he slowly got to his feet and walked
toward me, step by step. His eyes never left me. I could feel his gaze as it
jumped from my face to my breasts, from my feet to my crotch. He was hooked.
He muttered, "God, I didn't expect you to be THIS beautiful."
              He had made opened a magnum of champagne and deftly poured each
of us a drink. Still, he never took his eyes off me. The champagne tickled my
nose but warmed me inside. He poured another. I intertwined our arms with the
glasses in it. We drank as lovers drink. He had put unchained melody on the
stereo and we danced again. But this time I lead and Sam had no objection at
all. I led us toward the bedroom. He got the hint and took over. As we entered
the room, he kicked the door closed with one foot, never missing a step. The
music magically ceased as we reached the bed. Sam suddenly wrapped his arms
around me, hugged me tight and kissed me. I felt his breath across my upper
lip. Then I opened my mouth slightly and he slid his tongue in and out,
teasingly. I opened it wider and he forced his tongue in deeper, filling my
mouth. As he probed, I started to unbutton his top button. Understanding my
motion, he released me enough to continue my way down his chest. I unbuttoned
the last button and ran my finger through his coarse chest hair. It was
heaven! His chest was lean and firm, not rock hard (like my cock right now),
but very strong. I pulled the shirt off his arms and threw it on the floor. We
then broke. I gently pushed him back and he sat on the bed. I slowly sank to
my knees. I undid his belt and pulled down the zipper. I could now see the
massive lump in his underwear. Probably for the first time in my life, I found
white, cotton jockey shorts sexy as hell! I reached out, not at all
tentatively and grasped in firmly in my hand.  I pulled and pushed a few times
and got great reaction from him.  I released his manhood and pulled his pants
off. I then slowly crooked a finger into the elastic band and gently started
the long trip down for his jockey shorts.  There. I had exposed his throbbing
cock. It was actually straining at me.  Without hesitation of forethought, I
pulled the shorts off and sunk my head into his crotch.
              I flitted my tongue like a snake at the smooth head. I could
taste salt. The penis seemed to keep getting larger and larger. I slid my
lipsticked mouth over the hood and into the shaft. The lipstick provided a
very good lubricant as i took more and more of the shaft into my mouth. I felt
myself start to gag a little, so I backed out a little and then proceeded.
After a very short time, I had him all the way to the back of my throat. He
tasted wonderful! The salt mixed with the natural skin to create a delicious
dessert. I started to move my head back and forth slightly, then a little
quicker. I could hear him moan a little. I started to go faster and faster,
sliding my tongue all around the cocksickle in my mouth. I felt him stiffen
quickly, and then felt the rush of cum into my mouth. I was able to get my
tongue on it as it shot out and it was creamy and warm and made me warm all
over. Finally, he relaxed. I cleaned up his cock with my tongue and released
him . I slid my tongue across my lips and looked up at him. Only one thing
crossed my mind. In a very sultry and suggestive voice, I stated, You ain't
seen nothin' yet.

******************************************************************************
 So ends Part three of my great adventure with Jake. PART 4 will available
hopefully later this week. I need to go take a very long, very cold shower
now!

                    Hugs and Kisses,
                         Jo Black


                 JAKE PART 4
                              BY
                           JO BLACK

In which things get stickier and stickier as I attempt to
decipher what has happened and determine what will occur.


              As I sat on the floor, my head in his exposed lap, I felt spent.
Never before had I experienced such great exhilaration during sex without even
being touched. I believe that is a result of the knowledge of giving such
exquisite pleasure while being in total control of the entire act from
beginning to end. I will always relive that moment when Sam reached climax
while I took, not accepted, but took his love in my mouth. Perhaps the
greatest thing about being female. You are at once demure but forceful; you
crave security but control; you are beautiful and delicate, but are in charge.
I wonder when all this great philosophy has occurred to me. Maybe I always
knew it subconsciously but repressed the knowledge because I was living a
masculine life. Not any more! I am woman, hear me roar.
              Sam recovered slowly and started to pull me toward him. I cooed
softly, "Not now Baby. Just lean back and relax." I gently prodded him
backwards onto the bed. I then pulled myself next to him and started to
massage his chest. Everytime he tried to reciprocate, I gently but firmly
stopped him. I now knew control; I was hardly ready to relinquish it. I worked
my self lower and lower down his torso. I moved my head onto his chest,
knowing that the wig hair was now tickling his skin. I paused briefly at the
navel and slowly licked and tongued it. I felt his muscle ripple and stiffen.
I silently glided my hand down until I contacted his coarse pubic hair. I
found and slowly rolled his balls in my hand, just like Captain Quegg in The
Caine Mutiny. Sam started to moan and slide his body from side to side. I
continued to massage and kiss and tickle; not giving him a chance to do
anything but rebuild his expectations. I then continued to flow down his body,
trailing my hair across his now nerve heighten belly. I reached his cock and
grabbed it with my free hand. I saw the long, red nails resting on the shaft.
I then traced the nails ever so slowly up and down the shaft. The cock grew in
front of my greedy eyes. It thickened then extended itself. I kept dragging
the red nails up and down, up and down, up and down as the blood started to
engorge the rockhard cock. I knew that he was good for a while because I could
still taste the salty, creamy cum in my awaiting mouth. I released his balls
and brought my hand below him, again, agonizingly slowly, letting his every
nerve be stimulated by my touch. I stuck out my finger and inserted it's
sharp, dart like nail into his ass. He stiffen the muscles upon first contact,
but I persisted to slowly grind the finger deeper and deeper into his rectum.
Suddenly, he relaxed and I then drove the finger into his prostrate and then
Sam really moaned. I backed off and then jammed it again. I repeated this and
Sam really responded. He was ready to come but quite frankly was still spent.
What I delightful time I was having!
              It's funny, but while I was tending to Sam's needs, I never got
hard myself. As I continued to manipulate the balls in one hand and tend to
his asshole with my other, I marveled on this. I was quite satisfied at this
point with just the emotional release. I have read many things about orgasisms
being as mental as physical. Evidently, this has a lot of truth to it. Enough
analyzation; back to thee task at (or in) hand. I could feel him go even
harder in my hand. I instinctively knew the time was right. I pulled my finger
out of the rear and slid my head back to his steel shafted organ. I ran my
tongue down the top and up the back. I slowly licked the entire crown of the
hood. I then started to suck it in like a strand of spaghetti. As I slurped it
into my mouth, i gently worked my tongue across the breadth of the now
seemingly enormous organ in my mouth. I could taste the sweat mixing with the
precum. I sucked harder and harder. This time, it felt like I was swallowing
the head of his cock. I just tried to relax my throat and then he came. It
seemed like a tidal wave had hit my tonsils. The relentless attack by the wave
of cum seemed to last forever. I felt him relax. I disengaged from his groin
and moved up his chest and gave him a great big kiss, wet with his own seminal
juices. He just hummed with delight. I must have ingested a quart tonight, but
it was unbelievably erotic.
              I must have dozed off for a few minutes when the phone rang. Sam
answered it and turned to me and whispered, "It's Jake. Do you want to talk to
him?" I nodded yes.
              Jake wanted to know my plans for the rest of the evening.
Feeling drained from my experiences, I told him I would be ready to leave in
about 20 minutes and would meet him in the bar. After I hung up, Sam laid on
the bed with a scowl on his face.
              "Is there something wrong?", he asked. "I thought everything was
perfect; at least I KNOW it was for me. What can I do to change your mind."
              I had sort of planned on this happening. "Sam, everything was
great; better than great. It's just that I'm tired and I need time to think
about what has happened and exactly how I really feel about it. To be
completely honest, this entire evening was 100% better than I could have
possibly imagined. Besides," I vamped, "if I stay here, I sure won't get any
sleep."
              Sam nodded, "I think you could be right. Let me offer this. I
need an assistant manager right now. I will pay you handsomely and provide
your wardrobe. And this is a real job. There is too much for me to do alone. I
need someone I can trust and like to spend time with. Don't say anything yet.
Think about it. If you decide yes, come in tomorrow. If not, thank you for the
best night of my life." He kissed me deeply and soulfully and then released
me. I quickly donned my red minidress, that venerable garment that made this
night possible and left to meet Jake downstairs.
              I found Jake on a bar stool in the now empty bar. The lights
were fully on and in looked like an empty theater after a play. I slid on the
stool next to Jake and he said, "Man, you OK?"
              I responded quickly. "More than OK, I'm better than I ever have
been. I'm a little confused but I'm happy. Come on old buddy, take a lady
home." He nodded and we retraced that earlier trail to his car, now the last
in the lot.
              We drove in silence for a while. Finally, flirtingly asked,
"Don't you want to know what happened? Huh, Huh, come on, it's got to be
killing you."
              Jake's eyes recovered their sparkle. "Yea, got lucky, did you?"
              "A lady never kisses and tells, big boy"
              "Well", he drawled in a newly found southern accent, "you shore
are right, Ma'am. Good thing the only ones here is a man and a filly."
              I couldn't help laughing. Jake's attitude had returned to the
old sense of humor. We quickly traded notes on our latest adventure. It was
just like always. He did this, then I'd top it. This comradierie continued all
the way home. Pulling into the garage, and with a great flourish and an awful
British accent said, "May I take your hand, M'Lady."
              I, in reaction, offered my hand and he gentlemanly assisted me
from the car and closed the door. He in turned opened the door to the kitchen
and allowed me first entrance. I could feel his eyes on my now practiced
wriggling walk. I purposefully exaggerated the swagger of my hips. I put one
hand on my hip and almost taunted him as he followed back to the bedroom.
After we entered, I turned to him and said, "Why don't you come up and see me
some time?"
              He just laughed and we entered the bedroom. I sat on the edge if
the bed and Jake sat next to me. "Did you really enjoy it?", he wondered.  "I
mean, did this evening open any doors or at least resolve any conflicts you
had?"
              I reached over and took his hand, rather shyly I might add.
"Jake, You don't know what a favor you did for me with this evening. I hadn't
thought of this since High School. Not because I didn't want to, I think, but
because I just plain blocked it out. I answered some questions tonight. I like
wearing these clothes and being feminine. It's just right for me. I know now
that I am attractive and I want more. But There were new questions brought up
tonight I just don't know about. The sex thing really threw me for a loop.  I
was never more turned on and more satisfied in my life than I was with Sam.
But I don't know if this means that I am simply Gay, or if I'm really female
having straight sex. I'm really confused over this. Tell me, what do you
think?"
              Jake pondered all this for a moment. He then glanced down at my
hand in his and said, "I think that it doesn't really matter. Look at it this
way; you and I are friends. But you are holding on to me for dear life. In the
past, we would never had made physical contact like this. But I don't feel
it's strange and you don't either. But are you Gay; are you female; I don't
know. I suggest you take that job at the bar. Give it a chance. Don't be
scared of what happen tonight nor let it sweep you off your feet. Your
consulting business can function without you for a while. You told me that.
Call and tell them you're on a sabbatical. Move out of the company apartment
for a while. Hell, move in here with me. I'll help you explore all this. It
will be just another grand adventure."
              And that's just what I agreed to do. A neutral ground is a much
better atmosphere to make decisions. I asked, "Just where do I sleep. You only
have one bed and your couch is lumpier than Mom's mashed potatoes."
              "Well, I guess in here with me. Hell, we've done it a million
times in the past."
              This seemed quite innocent on the surface, so I readily agreed.
His couch was impossible to sleep on unless you've passed out on after many,
many drinks. I then realized that I knew WHERE I was going to sleep, but
didn't have an idea in what I was going to sleep. Good ol' Jake to the rescue
again. "Man, I mean Jo, my sister has quite an extensive collection of
clothing here, including some of the wildest nightgowns you could imagine.
Just help yourself, they are in the hall closet. I nodded rather
apprehensively, but quite gratefully. I didn't really have to make this
decision and was quite glad about it.
              After rummaging through the closet, a rather large walk-in I
should explain, I was amazed at the selection. There must have been over 100
different garments hung up in there. These ranged from business suits, peasant
blouses, miniskirts to the most wonderful lingerie imaginable. I was torn
between a gorgeous white silk gown with a slit up the front and a navy blue
form hugging satin gown with no back and very thin straps. Finally, after my
earlier activities, I felt I wasn't entitled to wear white, I settled on the
other. I collected it and noticed a pair of dark backless, 4" heeled pumps on
the closet floor. I took my selections into the bathroom and got ready for
bed. I bathed rather quickly in the same bubble bath I had earlier. I was
sticky and smelled of sex. After drying off, I powdered my chest, legs and
genitals. I then let the satiny gown drift down, across my perfumed body.
Again, my cock rose to meet the challenge of the soft, sexy material as it
tickled my chest and flitted across my thighs. I then sort of tousled my hair
and it fell in that sexy, half askew, half curled look. I checked myself in
the mirror and was shocked. Here I was without a wig, no restraining
underwear and no makeup and I was still gazing upon one hell of a sexy looking
broad. Granted, the lights were a bit dim, but then, I thought, so am I. As an
after thought, I placed my breast forms in the front and the tight, clingy
gown held them in place perfectly. I ran my fingers across my thighs and
discovered that I still had those long nails on. Good. I turned sideways in
the mirror to catch one last look of my now sexy profile and entered the
bedroom.
              Jake had turned down the bed and was already under the covers.
The lights were low and the stereo played a little Dizzy Gillespe in the
background. I wriggled my way to the bed and kicked off my heels and swung
myself into the bed. By the way, it's a real bitch to keep a nightgown pulled
down so your privates aren't exposed. I lay on my back, just recalling Sam and
his offer. Is this what I really want? I know that Sam is really smitten with
me, or at least Jo. But before I can address that situation, I need to be more
sure of my femininity; is this for real or just a lark. I had never even
considered kissing a man before, let alone giving him what I feel was the
world's greatest blowjob! Well, there's one sure way to find out. I will take
Sam up on his offer. That means I can dress full time and be in public to
really see the entire picture. The other way to study this is close at hand.
              I rolled over on my side and ever so gently draped my arm across
Jake's chest. He said nothing, but his breathing increased. I felt the now
familiar stirring in my groin. Saying nothing, I slid my satin encased body
across the sheets and pulled myself up on Jake's body. I was getting harder. I
planted my lips on his lips and he immediately responded in kind. He flicked
his tongue in and out from between my lips. He pressed harder and I pushed
back. His hands found my smooth ass and he squeezed it softly and then harder
and harder. Suddenly, he rolled over and I was on the bottom! How many times
had I seen that move in High School wrestling? He was as strong now as he was
then. His hands began to explore my body, rubbing up and down, up and down.
Trapped under his weight, I felt a little panicky for a second. I wasn't in
charge as I was earlier. But I still liked it. I began to follow Jake's lead.
He would grind his hips, and I would grind his hips. Only I did it softer than
he. He was really getting hot! He began to pant and I could feel his hot
breath on my neck while he nibbled at me.  I felt like I was trapped and it
felt good, kind of secure and wanted. He turned me over and started to massage
my ass. Suddenly, he raised the skirt of the nightgown and I could feel the
strength of his hands as he rubbed me. I heard a door open and I turned
around. Jake had opened the nightstand and removed a tube of KY Jelly and a
rubber. I propped myself up and took the package from him. Opening it, I
pulled the rubber out and pulled down his red cotton briefs. I had forgotten
how huge he was! His cock was already standing at attention when I coddled it
in my hands. I inexpertly slipped the rubber across the rubber, only after
kissing the head. I could taste the salty precum and I wanted him!
              Jake then opened the jelly and smeared it on the rubber. Oh, oh,
here was a new experience. Well, I was so hat by this time, I would do
anything. Besides, after tonight, I don't think I'll be easily shocked. He
rolled me back on my belly and lifted up the skirt. I felt the shock of a
great glob of the jelly being shoved up my ass. It warmed quickly and was
rather pleasant. Jake laid on me and started to tickle the inside of my thighs
with the slick cock. He pulled my up onto my knees and I knew it was showtime.
Thank God. I wanted and I wanted it now!
              Then I felt it. The tip of the now metal rod was throbbing in
anticipation. It started to slide through the jelly and I then felt the pain.
It shot through my body like a knife. Jake, evidently sensing this, withdrew a
bit and then gently began to reinsert the cock into my ass. As it went deeper,
the pain began to subside. Jake continually pulled back and then gave me a
little more. Over and over; it was like I was being reamed out to fit his
throbbing manhood. I forgot any discomfort as he completely filled the canal.
I was almost pinned like a butterfly on a mat. It was exquisite! My body began
to move toward his thrusts and I felt myself lose control completely. The cock
now slid back and forth and back and forth; easily, with just enough
resistance so we were both reaching higher degrees of ecstasy. Then one last
desperate plunge contacted my prostrate and I came. "At exactly the same time,
Jake also let go. I could feel the hot, rushing cum as it filled the rubber
up.  Jake grabbed my  organ and let my seed fill his hand. We must have
ejaculated for several minutes it seemed. Spent, he withdrew from me and we
rolled next to eachother. He brushed his cum soaked hand across my lips and I
tasted myself for the first time. I smiled. Jake then licked off his hand and
grabbed me and just held me. We slept that way, intertwined. We both had
things to think about and resolve concerning our friendship, but not now. I
felt warm and sticky and just about perfect. I slept.  I'll worry about that
tomorrow.

******************************************************************************
 This concludes my first date. If there is any interest in continueing this
series, please let me know. If not, I'll start a new series soon.

                                  Ta-Ta,
                                   Jo