Archive-author: Jo Black
Archive-title: My Friend Jake
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
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.
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,
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
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
I then asked, "This bar you want to go to tonight; is it a regular hangout for
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
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!