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My Friend Jake
by Jo Black (1998)

***

Two guys get involved with gay sex, cross-dressing and 
submission, one for the other. (MM, 1st-gay-expr, d/s)

***

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 upon. 
They are always odd but extremely interesting. 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 cross-dressing. 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 whatever 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 
mini-dress.

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 mini-dress 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 incredibly 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 jaw line. Then I 
worked with the blush and powder to highlight my cheeks. 
The eye shadow 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 judgmentally 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. Whatever 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 
mini-dress, 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.

***

 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 sports coat; in my red mini-dress, 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 forever. 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 its 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 beach bum 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 cross-dresser. 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 an 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 every time. 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?

Sam led me back toward the bar. I followed defeated. 
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. 
Unfortunately, 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 of myself as 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, "B-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 
whatever 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 lightning 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 my 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 its 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.

END

* * * * * * * * * * * * * * * * * * * * * * * * * * * *
It's okay to *READ* stories about unprotected sex with
others outside a monogamous relationship. But it isn't
okay to *HAVE* unprotected sex with people other than
a trusted partner. 4-million people around the world 
contract HIV every year. You only have one body per 
lifetime, so take good care of it!
* * * * * * * * * * * * * * * * * * * * * * * * * * * *
Kristen's collection - Directory 68