Date: Tue, 4 Jan 2011 20:56:45 -0800 (PST)
From: Chuck Hughes <k56gh76@yahoo.com>
Subject: Learning to Please - Part 7

This is a true story; If you are not 21 or over do not go any further.  If you
do not like man on man sex go no further.

Learning to Please - Part 7

Howard and I did not go out for dinner - I wasn't ready to merge my real life
outside with this fantasy world we had.  I felt weird, confused and wanted to
leave.  I hurried to leave explaining that I had tests to study for, but that I
would call him.  My ass was sore and the train ride back to college seemed
particularly bumpy.  As I sat there, I recalled everything we had done, and
thinking about it made me feel very horny.  I looked at dozens of men going
about their commute with blank, dull faces, their minds elsewhere.  Inside I was
glowing with the thought that I had literally gotten down on my hands and knees
and gave a man my mouth and ass - I gave a man sexual relief and he thanked me
for it.  Part of me wanted to turn right around and ask Howard if I could sleep
over.  Part of me thought that would be pathetic and I had better get control of
myself.

I spoke with Howard a few times over the next few weeks.  I had had a great time
with Howard, but was becoming nervous.  Nervous about what I was becoming.
Nervous about getting found out.  I questioned if this was who I really was -
was this something I wanted to become?


I continued with my assplay and submissive fantasies while masturbating.  But
afterwards sometime I'd feel relieved and relaxed, and other times guilty and
embarrassed.  I buried myself in my classwork and forced myself to have a few
non-committal phone calls with Howard.

I think Howard sensed that things were changing between us and it became
awkward.  Howard said he picked up some new things for me to wear and that he
was anxious to see them on me.  I gave in one day and agreed to meet Howard at
his apartment Friday around 7 o'clock and make a fun night of it.  Howard told
me that he'd be working late, so that he'd leave the key to his apartment with
the doorman for me to pickup.  He said, that way I could let myself in anytime
and dress and get ready for him to arrive.  It sounded fun and I was quite a bit
aroused with the thought of getting to his apartment early and dressing up for
him, and just walking around his apartment waiting for him to come home and have
sex with me.

After my last class, around 2pm I started taking the train to Howard's
apartment.  When I arrived I spoke with the doorman, giving him the same false
name I had given Howard when we met.  He asked if I had ID, and I told him,
sorry, but I forgot my wallet.  He seemed a little doubtful, so I suggested that
he could call Howard at work.  He handed over the key with a shrug and I took
the elevator up.


Once I entered the apartment I locked the door behind me and took a cursory walk
through the apartment.  It was clean and neat, and Howard wasn't home yet.  In
the guest room, my room, I found a shopping bag with a few packages in it laid
out on the bed, and a card.

I opened the card to read:

"Dear Christine,

I'm glad you were able to make it over to spend time with me tonight - it will
be a lot of fun.  You'll find a few new items here for you to wear, which I hope
you like.  I'll be home promptly at 7 and I would really love it if you greeted
me at the door with a freshly made martini.


Thank You - hugs and kisses (on your bottom),

P.S. You'll find a new wig I picked out for you on the vanity in your bathroom,
I hope you like it because I think it will look hot on you.

Howard"

Christine - my new name, his choice for me.  I walked over to the bathroom and
looked in at it, sitting on a Styrofoam head-shape.  It was a medium length,
curly hair style wig in medium chestnut.  I reached out to touch it and run my
fingers through it.  It felt a little plasticy, but it was very sexy looking and
I knew it looked better than my current hair style.  I found the box in a
shopping bag on the floor (it cost $85!) and read the instructions for care and
use.  I ran the bath and went back into the bedroom, undressed and folded my
clothes and placed the neat pile in one of the empty dresser drawers.

I looked at the bag on the bed but decided that I had plenty of time to go
through the packages, and that first wanted to soak and relax.  I wanted a
drink, so I put on a short pink satin robe that was hanging in the bathroom and
started for the kitchen.  I stopped at the doorway, paused and walked over to
the closet and found my box of high heel shoes.  I slipped them on and looked
down at my long, thin legs - glad that I had decided to keep them shaved.  I had
even shaved most of the hair and peach fuzz off of the rest of my body.  All
that remained, aside from the hair on my head, was my underarm hair, and a small
patch at the top of my pubic area.  Although I had taken the time to carefully
shave the light hairs from my scrotum, ass-cheeks and underneath, I liked to
keep this small patch of hair at the top of my pubic area, which I liked to run
my fingers through.

Sitting on the bed I crossed and uncrossed my legs, looking down at my feet and
admiring how nice my legs looked in the open toed shoes.  I opened my robe to
observe that, although my small nuts seemed to tingle with anticipation, my
small cock had shrunken to it's smallest, softest, form - almost as if it had
moved back into my body.  I went through my dresser drawers to find a pair of
panties and slipped them on.

Remembering the bath, I carefully walked back to the bathroom and turned of the
water.  The bubbles were piled high and the water was very hot.  Now for that
drink.  With the robe hanging open I walked to the kitchen - slowly, getting
used to the heels - and took mental inventory of the refrigerator contents.  No
champagne.  Darn it!

I walked over to a piece of furniture my family referred to as a 'tea cart',
which I expected to hold bottles of liquor.  I was right.  I took inventory of
the contents and was glad to find a small book with drink recipes.  I found the
ingredients for the martini and set them aside.  With the bottle of vodka in
hand I went back into the kitchen and fixed myself a nice tall vodka and orange
juice, and gulped half of it down, and then refilled it.

Drink in hand I wandered through the apartment, trailing my hand along the
furniture and the walls, somehow wanting to touch and not be afraid, not like a
visitor to a museum, but like this was a place where I was welcome.  I stood
outside Howard's bedroom, leaning on the doorway looking in.  Before I came over
today I had already decided that I wouldn't snoop through Howard's things.  He
was trusting me by making the key available to me and I didn't want to break
that trust.  The room was neat and the bed was made, but some of the dresser
drawers were partially opened, as were the closets.  From the hallway I could
see into his master-bath and see that towels were hanging and the vanity was
covered in his grooming products.  I reached down and pushed my small nuts back
between my legs as far as I could and crossed my legs tightly to hide as much of
my boyhood as possible.  I imagined standing there and posing for Howard, and
him looking at me with lust and need, like he had the last time we were
together.

As I stood there my left hand came up and cupped my small, flat right breast.  I
sipped my drink as I touched and teased my breast and nipple.  I was transfixed
staring at Howard's bed, wondering if he'd make love to me in his room tonight.
I didn't want to think about it, but with jealousy I wondered about how many
other women or boys he had enjoyed in his apartment.  I started to fantasize
about standing there watching him from the doorway as he thrust his cock into
another woman, the woman arching her back under him, her heavily lacquered nails
digging into his shoulders and back.  I imagined them hugging afterwards and
laughing.  As he rolled off of her, I'd see her propped up on her elbows, legs
apart with Howard's cum oozing from her.  With a friendly grin she makes a
slight nod of her head, inviting me to come over, and as I approach she spreads
legs a little wider and playfully asks if I 'want some?'.  As they both watch
me, I carefully crawl onto the bed and place my face into her lap, extending my
tongue, and taste both of them.  She purrs warmly as I clean her, and then
switches to a mocking tone, telling Howard, 'Ohhh, she is good Howard!'

I closed my eyes and tried to clear the scene from my mind, and took another
long sip of my drink.  I left Howard's room and went back to my bathroom,
stripped and sank into the tub.  I soaked and relaxed until the water was cool.
I rewarmed the tub and finished washing, paying special attention to my bottom.

I dried off and put the robe back on, anxious to see how I looked with the wig
on.  I felt a little nervous as I lifted the wig from the mannequin head and
felt it in my hands.  I looked at myself in the mirror trying to raise the
courage to put it on.  I searched through the vanity to find the lipstick I had
used before and put it on.  It took a few attempts again, but finally I had
attractive lips.  I scooped up the wig, closed my eyes and bent over and flipped
it onto my head.  Keeping my eyes closed, I turned my back to the mirror and
tugged and adjusted the hairline until it felt right, and felt sure that none of
my hair needed to be ticked in.

I slowly turned around to see how I looked.  My heart skipped a beat - I looked
feminine and...beautiful.  I immediately saw areas for improvement - my
eyebrows, perhaps some colored eye shadow, but I smiled at myself and was quite
happy.  I looked cute, hot, and knew Howard would be happy with his selection.

I went into the bedroom to look through the packages Howard had brought for me.
The Neiman Marcus shopping bag held several gift boxes of different sizes.  The
first box held a neatly folded silk blouse, which I laid out on the bed.  It was
light pink, and the tag told me it was a "Petal Sleeve Cowl Neck" top.  I
remember gasping when I saw the price tag showing that it cost more than $200.
It was beautiful and the cowl neck seemed like it would plunge quite low on me.
I liked it.  Also in the box was a very thin silver metallic belt, which I
imagined was supposed to be worn over the blouse at the hips, event though there
were no belt-loops on the blouse.  The belt (more like a fine chain) was very
long and I guessed the style was meant to be left with a long piece hanging.

The next box was a shock - a pair of long, tight black disco pants in a shiny
material.  My heart raced as I imagined myself wiggling into them and looking
like Olivia Newton John did in Grease!

A smaller box held a pair a black panties, a note card and a small sealed
package.  The note was from Howard, telling me that he thought I'd look very
sexy in the tight pants, but that I would probably feel more comfortable if I
lined my panties with a woman's pad.  I quickly realized that this might help
smooth out any unsightly bulge my boyhood might made.  That was very thoughtful
of him and I was anxious to try it and see how it looked.

The note had a postscript:

"P.S. - I did my best with the shopping for you, but there is one last item I'd
like your help with if you have time.  I'd love to see some nail polish on you,
but didn't know what color you would like best.  Would you be a doll and take a
quick trip to the drug store on the corner and pick something out to try?  I've
left money on the coffee table for you"

My heart was racing again...it seemed so sexy, going to a store to buy nail
polish to paint myself for my man...wearing this absolutely hot, slinky outfit,
that gorgeous wig...sitting here waiting for 'my man' to come home....

I was in such a hurry to leave I almost forgot the last box.  A shoe box - my
size.  I ripped the lid off to see an outrageous pair of high heeled stilettos
with a cheetah print.  The outer material was velvet and the foot-bed was a tan
padded suede.  I actually felt my small cock twitch as I ran my fingers along
them.  He was going to have me dolled up like a young, thin, Peg Bundy.  He was
probably going to insist on me wearing the shoes to bed, or maybe even take me
standing up in them...

I was flushed and feeling dizzy.

End Part 7