Date: Fri, 11 May 2001 21:54:25 -0700
From: Ciana <cianatv@hotmail.com>
Subject: Helping Jim to Relax Part 1 of  2 (M/M, passionate, oral, anal, TV)

PLEASE NOTE: This story is fictional and involves sensuous sex between two
close friends. The characters exist but the events have not yet transpired.
(Emphasis on yet!)
Let me know what you think! Submitted by: cianatv@hotmail.com



Jim and I were best friends off and on growing up, sometimes though maybe
because I wasn't quite cool enough in some ways, or perhaps just a
convenience when he didn't have someone else to hang with he would call me.
He was 18 and I was 16 when we first met, intellectually we were equals.
When it came to the fairer sex though, Jim always had a leg up on me it
seemed. The girls seemed to go for his wacky sense of humor and yes good
looks. I was no slouch mind you, at 5'9 and 140 lbs, but the blue eyes,
chiseled face, and 6'0 well built frame that Jim had ensured he was the most
sought after guy I knew. Though he was my best friend at times I felt rather
jealous of the attention that he would give to the girls. Especially, so if
he and I had made plans to catch a movie, or just hang out and he cancelled
at the last minute with some made up story of working, or chores around the
house.

Sometimes he just wouldn't show up at all, without even a call. I knew that
this wasn't fair, and that at these times he would rather have a girl to
hang with than me, but I also could tell that the bimbo types that he was
interested in were only after the status of saying that they had dated him
for bragging rights with their girlfriends. Inevitably, I would always get
the call, the "hey man I just got dumped, you want to grab a pizza call." Of
course, I'd say, why not? Even though I was pissed off because of the way he
had just blown off any plans we had made for one of these chicks, I would
still be the comforter. I was the guy who always said: "Don't sweat it man,
she'll either come back or there will be someone to take her place." What a
best friend, yeah right! Secretly I was saying I told you so under my
breath.  Well shortly after one of these episodes, Jim met another girl
named Chris. What a bitch I thought! She was too perfect a school boys wet
dream. Perky tits, short skirts all the time, and a cheerleader too. She was
also a slut who didn't care about Jim at all, and I knew it wouldn't last.

One Saturday morning Jim called, his parents were going out of town and he
wanted to know if I could hang out for the weekend, maybe we would hook up
with Chris and one of her friends, and see what happened. I hadn't had a
girlfriend of any caliber for about 2 months at this point so I thought this
would be pretty cool. Sure! I said I'll be there around 2:00. I grabbed a
pair of jeans and a shirt, stuffed into my bag and headed over to his house.
I arrived at about 1:30, and Jim's car was gone. So I figured that he was
out getting some food or something. I knew Jim's family very well, and they
trusted me enough so that I was the only one of Jim's friends who knew where
the spare key was at so like I had done on other occasions I let myself into
the house and waited. Well at about 2:30 I was starting to get agitated, by
3:00 I was pissed off, I started to leave when I said to myself, that I
might as well enjoy the house, and so I started to explore. Mind you I had
been in Jim's house dozens of times, but this felt different.

First I went to his room, which is where I usually slept in his older
brothers bed, across the room from Jim's. His brother had gone to school for
avionics and was a mechanic for TWA out on the East Coast at LaGuardia. I
quickly unpacked my clothes and stowed my duffel bag. I walked by Jim's
parent's bedroom this room was the bomb! It had huge walk in closets a King
Size Bed, and of all things a hot tub in the middle of the room.
The hot tub of course was always off limits for Jim and I. However with Jim
nowhere in sight, and his parents gone for the weekend, I felt that I was
deserving of a little luxury. Why not!? So I started to look for some towels
and then I found my way to one of the closets in the room. It belonged to
Lynda, Jim's mom. She was older and definitely a conservative woman, but I
still always found her to be both funny, and rather attractive at the same
time. I of course was a teenager with raging hormones so what else are you
going to think about your best friends mom. In any case as I was looking for
towels I couldn't help but notice the large quantity of clothes that Lynda
had. Jim's dad was an estate planner, so with many very wealthy clients
there were lots of very formal dresses and gowns for special events, and
charity dinners. Then I saw it in the back corner, a black, halter style
dress that was only long enough to flirt with the top of Lynda's knees, if
it came down that far. I didn't know she had it in her, but I guessed from
the fact that it had a dry cleaning ticket that was at least 6 months old it
had been some time since she had worn it.

Well I picked it up and for some strange reason held it up next to me and
stood in front of her floor to ceiling mirror hung in the closet. (Just to
see how far it must come down on her, of course) Lynda was about an inch
shorter than I was, so I figured it must come just to her knees. Then a
really strange though occurred to me, I was sub consciously trying to
determine where it would fall on my legs. I figured that it would probably
be about 2 inches above my knees, while I was thinking about this I was
shaken out of my daydreaming by the sound of the telephone ringing. I
dropped the dress and went to pick up the phone, just as I thought it was
Jim. Gary, I figured that you would be there by now. Yes I am, and I figured
you wouldn't be, I snapped. Hey ease up man, Chris just dropped me for some
guy who works at the mall, I'm dragging. I almost jumped for joy, but I had
to control myself. Where are you now? I asked. I'm up in Kenosha leaving the
mall. Kenosha! Why in the world did you tell me to be here this afternoon,
if you were going up there? Hey Gary she said that she needed to get
something that she had put on hold at the store, she called at the last
minute and I took her. When we got there she left me cold and went home with
this other guy.

What did you do? I freaked, I felt like driving my car into a wall, or
something. This was serious, I thought. Look Jim, why don't you come back
here we'll grab a bite and work it out. I don't know, he said I can't eat
anything now. Good I said, I'll find something here and make us supper. Now
just come home. Okay Gary, but you know I'm swearing off women for a while I
can't trust them anymore, I, don't want a relationship. I just want to get
laid and often by a women who won't screw with my head. Yes, I know, well
just get here, and be careful man. As I hung up the phone it occurred to me
that he was really in a bad way this time. What could I do? I then had the
weirdest thought. What Jim really needed was some levity, some comic relief.
No! What Jim really needed was female companionship. Now who could I call.
Wait a minute, what if just for tonight Jim had dinner with a woman who
would have a sincere interest in him? What if that woman knew him better
than any one else? What if I became that woman? Whoa! I said to myself, you
must be crazy. But the I said, like so many other times when Jim was
concerned...Why not?

I went back to the dress that I had dropped on the floor and laid it across
the bed, hmm, this would do nicely but I would need more than just a dress.
What would Lynda wear with this? Stockings, probably a garter belt, and
definitely shoes, but not flats heels. This might be a problem, well I went
about her belongings like a mad man, soon to be mad woman. Finally I had
gathered a pair of black panties, a matching garter belt, and some very
silky thigh high stockings. I next went to Jim's room remembering a play
that he was in a few months ago where he had to play the part of a
headmistress in school, and was required to wear 2 1/2  inch black heels. I
was sure he had bragged about having kept them just to get Ross the wardrobe
guy in trouble with the school. I went to his room where the secret stash of
gin, and playboys were kept, and right behind the magazines I saw a pointed
toe of a shoe, next to it was it's mate. Black shoes, stockings, panties,
makeup. Yikes, no makeup! Looking at the clock I knew that it would take Jim
at least another hour to get back home even with his lead foot. So I went
back to his parents room, and went to the little vanity table where I found
the cosmetics Lynda had left behind.

I quickly grabbed a foundation, some lipstick and eye liner and put it on
top of the table in front of the mirror. I then headed over to the shower
and turned on the water, I took a razor from the sink and some shaving cream
and quickly shave all the body hair off my legs. No big task, since I hardly
had any hair other than my shoulder length black hair which I wore in a pony
tail.
After I shaved and then showered, I put on some scented powder all over my
body and took a look at the clock, I had about 30 minutes left at the
outside, so I knew that I had better pick up my pace. I sat down on the edge
of the bed and put on the panties, carefully tucking my package away between
my legs. Then I slowly slid the silky stockings onto my legs, by now some
familiar stirrings were beginning to take place. Hold it together, Gary I
thought to myself, there's no time for that now. I next put on the garter
belt, and then I sat down at the vanity table and began to apply some
makeup. Luckily for me, the last girl I dated Karen was the makeup artist
for the school so I had watched her apply it before to other girls, dozens
of times. I did find however that it took me longer to get the coverage I
wanted without the gaudiness. I eventually did my eyes with a deep, blue
eyeliner, and matching mascara. Then came the lips, the only color that
Lynda had left behind was an unopened fire engine red lips color from cover
girl. It would have to do I thought. I next put the dress on and combed my
hair out. Finally came the shoes, I delicately slipped my feet into them, a
perfect fit. Now for the first moment of truth, I was going to look at my
reflection for the first time dressed as a sexy woman. As I approached the
mirror I tried to remember that no matter what the outcome the reason that I
was doing this was to help Jim.

All I could say was HOT! When I saw the reflection I almost forgot that it
was me and I wanted to ask this creature out. My legs were long and slender,
and just as I had thought, the dress stopped 2 inches above my knees. I bent
forward and my hair fell around my shoulders and I purred playfully in the
mirror, you want some of this don't you baby. When I said that my silk
encased penis throbbed and I wanted to take it out right there but I waited,
as I didn't want to spoil the look. Well next I cleaned up the room a little
and went downstairs to the huge kitchen to find something for dinner, after
all I did promise to make something. Opening the refrigerator I found a
couple of steaks and a pre mixed salad, so I turned on the range top grill
and got the steaks going right away. A bottle of merlot beckoned to be
opened so I found a cork screw and poured 2 glasses. As I did the front door
started to move Jim was home, I felt a lump in my throat but figured that it
would pass. What would I call myself? I was always partial to Kelly. So
before the door could open I ran and perched myself at the top of the
staircase, so that he would get a good look as he came in the door, but
especially at my legs. The door opened and then Jim walked in calling out in
my most breathy and feminine voice I cooed, is that you honey? Jim got a
puzzeled look on his face and then looked up the stairs, and as his eyes met
mine he was definitely changing his expression from surprise, to lust.

Gary? He's not here right now I'm his sister Kelly, and he asked if I could
look after you a bit. Is that okay? I said as I batted my eyes at him, ah
yes, that is, um that would be fine. I started to relax with the notion of
the powerful effect I had on Jim. I slowly descended the staircase and just
as he was about to ask a question I gently brushed my hand across the front
of his pants. My my, I said is there a little problem here...

To be continued...
For more stories and to share yours write me at: cianatv@hotmail.com