Archive-author: Jo Black
Archive-title: My Friend Jake
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
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
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
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
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
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
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
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?