CHARLIE

	Charlie came over to pick me up we were going out on the town
to try and pick up some babes. It was the same thing we had been doing
on Friday nights for the past three months. Sometimes we got lucky
sometimes not. Charlie sat on the couch across from me I was in the
arm chair. I asked him if he would like a beer before we went out. I
came back with the beers and a shot of Jim Beam for each of us. I
noticed that he had picked up last years Halloween photo album and was
looking through it. I sat down next to him on the couch to narrate
some of the pictures. He had the book open to a picture of me in my
hookers outfit. Short black leather skirt, Leather halter top, Fishnet
stockings and four inch heels. He looked at me and then looked at the
picture and then at me and then at the picture again finally saying
"Dennis, Is that you ?" I blushed slightly and said "Yes." He said
"That is incredible you are absolutely gorgeous." I told him "I dress
up as a girl every year for Halloween, Would you like to see the
pictures." As I passed him the shot of JB. He downed it in one gulp
and took a drink of his beer. I got up and got the well looked at
photo album from the shelf and returned to sit next to him passing him
the album which he laid on the coffee table opening to the first page
where I was dressed as the Homecoming Queen when I was sixteen. There
were many, The bridesmaid, The Bobby Soxer, Alice in Wonderland, The
Hooters girl. After a few pages he turned to me saying "You are
incredible." As he looked me up and down. For some reason I looked
down noticing he had a raging hardon that was about to split his
zipper wide open. I have never had sex with a man before but I
suddenly wanted to wrap my lips around Charlie's cock, Pushing these
thoughts aside I asked him which one he liked the best he turned back
two pages to one I had done two years ago, The school girl. A lacy
whit blouse and a plaid knee length skirt. I had liked that one too. I
got a lot of male attention that night. Then I asked him "Have you
ever dressed up as girl before ?" He replied "No, But I once wore an
Ex girlfriends nighty for a few minutes before she tore it off me in a
fit of passion besides how could I compete with this ?" Pointing to me
in a cute little black and white sundress from three years ago. He
said "Are you a crossdresser ?". I replied "Maybe but I only go out
dressed like that on Halloween."  He then asked "What are you going to
wear this year ? Halloween is only a month away." He kept looking at
the pictures and looking back at me. I said " I have a lovely little
black Cocktail dress would you like to see it ?" He replied to Quickly
"Of course I would love to." So I walked back into the bedroom and got
the dress from my closet looking at all the dresses on the right side
of my closet you could almost believe a girl lived here. I also
grabbed the black pumps and garter belt and returned to the living
room. Placing the garter belt and Pumps on the coffee table I held the
dress up in front of myself posing I asked Charlie "What do you think
?" He picked up the garter belt feeling the silk and lace and replied
"I think you will look awesome I can't wait to see you in it." I don't
know what came over me as I looked at his bulging crotch and slowly
moved up until I was looking him in the eye's and asked " Do you want
me to put it on for you ?" He took a long drink off of his beer and
reached down adjusting his cock in his pants. I heard a slight quiver
in his voice as He replied "I would love for you to wear that dress
for me, But I may not be responsible for what happens afterward." I
took the garter from him and said this may take a few minutes. I went
into the bed room and quickly undressed going into the bathroom and
shaved all over I then pulled the rubber band from my pony tail and
bent forward at the waist brushing out my hair I flipped it back and
felt it fall tickling my shoulders reaching under the sink I pulled
out some curlers wetting my hair a little I strategically rolled a few
into my hair. Going to the dresser I selected and pulled on the tight
and skimpy lacy black panty's tucking my now hard cock back between my
legs. I turned looking at the mirror and got an idea. Gathering up the
silky undergarments I stepped out into the living room Charlie looked
up from the photo album caressing himself thru his pants his eye's
growing wide as he looked at me. As skinny as I am I have very large
tits for a man. I pulled the black lacy bra up clipping it in front
turning it around adjusting the shoulder straps and arranging my
tits. Charlie laid back to watch still fondling himself. Next I put on
the garter belt pulling up a chair I sat down in font of him and
rolled the sheer stockings up my legs passing the garter straps inside
the panty's I clipped them on to the stockings. For added effect I ran
my hands caressing my now very feminine legs. As I stood up I adjusted
the garter straps I reached up cupping my breasts. I then picked up
the silky black slip and pulled it over my head. The silky material
sliding over my lace covered tits coming down to caresses my stocking
covered thighs was just the feeling I had been looking for and the
reason for doing this. The added thrill of Charlie's lust filled
attention had me completely turned on. I asked Charlie if I could get
him another beer. He nodded yes and I turned to walk into the
kitchen. I could feel his eye's staring at my butt. I got his beer and
peeked thru the opening in the wall to see him reach into his pants
and stroke his confined hardon I reached down to stoke mine through
the silken panty's. Returning to the living room just as Charlie
finished pulling his hand from his pants. I gave him his beer telling
him I would be back soon. He still could only nod. Back in the bedroom
I pulled out the rest of my hair accessories and my makeup case
proceeding to the bathroom using the curling iron and a little hair
spray after removing the rollers I applied some eye liner shadow a
little blush and some red lipstick. The effect was almost complete I
unzipped the back of the dress and pulled it on zipping the back with
some difficulty I straightened my slip and then the hem I got the
pearl ear rings and necklace and my black pumps. Finally allowing
myself to see the results in the full length mirror. The girl I saw
looking back was gorgeous. Shoulder length reddish blond hair, Pretty
blue eye's with long lashes, Long shapely legs, Nice Tits and a pretty
face with full red lips, Wearing a very feminine Black velvet dress
with a short flared skirt. I could not resist cupping my breasts again
and running my hands down just to feel all the silky cloths inside and
out, What an incredible turn on. The girl of my dreams. I had the
feeling she was about to lose her virginity to Charlie. With practiced
steps I sashayed into the living room. Charlie rose to his feet his
mouth dropped open, I raised one hand and Pirouetted for him asking
"What do you think ?" He said "Oh my god, You are beautiful." I walked
around the coffee table to him. He said "I would give my left nut for
a girl who looked like you." Walking up to him reaching down I grabbed
him by the cock. For the first time I held another mans cock in my
hand. I said "Its not your left nut I want its the whole cock. Pulling
me close he kissed me full on the lips. I could feel his hands grab
hold of my butt squeezing me. The feeling of his strong arms feeling
me through the silken garments made me just about cum in my
panty's. Breaking the kiss he looked me in the eye's and said "I have
never kissed a guy before, Never mind my best friend. But you have me
incredibly turned on." This he did not have to tell me, I was still
holding his cock through his pants and started to slowly stroke
him. He continued "I have always had a fantasy of having a gorgeous
shemale. He reached up and cupped my breasts in his hands. I replied
"I also have never been with another guy before, But have often
thought of it but only when dressed as a girl and you look good enough
to eat." As I undid his belt and fly allowing his pants to fall around
his ankles. He pinched my nipples as I pulled his jockey shorts down
and allowed them to fall on top of his pants. His cock which was a
little bigger than mine was sticking straight out and pointing right
at me. I reached down and cupped his balls in one hand as I grabbed
his shaft with the other and slowly started stroking him grasping him
about the base I slowly stroked him to his silky smooth head a little
drop of clear fluid appeared at the tip. I dropped to my knees still
holding his cock looking up I could see him looking down with glossy
eye's. Pulling my gaze down I found myself face to face with my first
cock leaning forward I licked the drop of cum off of the tip. Charlie
gasped and I swear his cock grew an inch in all directions. Holding
the shaft tightly I took the whole head into my mouth and sucked as I
wrapped my tongue around it and started to bob up and down as I
stroked the part I could not get into my mouth. Charlie moaned "Oh god
that is incredible." I reached up and started caressing his balls. I
could feel tiny spasms racing down his cock. I took as much of it in
my mouth as I could. Charlie bucked his hips forward as he grabbed the
back of my head suddenly I swallowed the entire cock. Charlie moaned
"Yes suck that cock bitch take it all." I sucked back until I had only
the head wrapping my tongue all around it still stroking when he made
a grunting sound and bucked forward again. This time I let him fuck my
face. On the out stroke I sucked as hard as I could and furiously
stroked him with my hand. I knew I had him as I felt his cock grow
even bigger as his nuts tightened. He swayed on his feet as he said
threw clenched teeth "I cumming !!" He grabbed two handfuls of my hair
as he erupted into my mouth with surprising force. I was expecting to
spit it out but to my surprise I liked and swallowed every spurt and
hung on for the ride I could feel his balls spurt with one hand his
cock pulse with the other his cock head throb with my lips and tongue
and his cum spurt off the back of my throat. I was so completely
turned on I could not believe I was completely dressed as a beautiful
girl on my knees with my best friends cock spurting in mouth and
loving every spurt. I leaned forward and swallowed his entire cock
until his pubic hair tickled my nostrils and wrapped my lips as tight
as I could and sucked back. I thought he would blow out the back of my
head. He moaned "Oh baby, You beautiful girl." My own cock tucked back
between my legs was so hard trapped in the tight lacy panty's it
hurt. I spread my legs a little and wiggled my butt and it sprung free
of the panty's up into the silken softness of the slip. I thought I
would cum myself. Charlie finished his last spurt so I held his cock
and licked the head looking up into his eye's watching him
squirm. Finally I grabbed his cock by the base and stroked it all the
way to the tip getting a moan from Charlie and one last big drop of
cum on the tip of his cock which I reached out for with my tongue and
licked off . Charlie collapsed back on the couch. I moved forward
between his legs and leaning my tits against his cock he leaned down
and kissed me and said "That was incredible, Will you marry me ? Where
did you learn to do that ?" I answered "Natural talent, That was my
first from this end." I stood up feeling my throbbing cock bob up and
down into the silky slip peeking out from under my dress. Charlie
reached out grabbing hold of my cock pulling me closer he lifted my
skirt and pulled down my panty's while stroking my cock. I was already
on the verge of the biggest cum of my life. I looked down and he was
already half erect again. Letting go of my cock he pulled me down
sitting on his lap facing him and ran both hands up under my dress
until he was cupping both of my tits pinching the nipples pulling the
cup on the bra down he started to bite my nipple after a while he bite
the other one I could feel our cocks rubbing together after a
while. He stood me up again tickling down my sides stopping at my cock
momentarily moving down to caress my stocking covered legs. I was
threatening to cum at any moment. Finally he returned to my cock
gently taking the weight of my balls in his hand he steered my cock to
his waiting mouth with the other completely licking the head paying
extra attention to the dab of clear cum at the slit. I knew he did not
have long before a full scale eruption happened holding up my skirt to
see what was doing I ran my other hand through his soft short hair and
said "Lick that pussy Charlie." Wondering what a pussy would feel like
now, Or better yet with Charlie's fat Cock in it. Charlie looked up at
me suddenly taking most of my cock in his mouth while stroking back
with his hand he pulled back furiously while stroking all the time. I
felt as though I had stepped over a cliff. The sperm boiled forth,
Charlie held on for the ride spurt after spurt, Charlie told me latter
I screamed as I grabbed hand fulls of his hair and drove my cock all
the way down his throat. He continued sucking and swallowed every
drop. Waves of passion cascaded through me, My cock seemed to cum
forever. Finally conscious thought returned Charlie had me by the legs
and laid me back on the couch looking up I smiled and said "Where did
you learn that? Will you marry me ? That was fantastic." Charlie said
"I can take no credit for that." As he leaned down to lick the last
drop from my cock head, Sending little electric charges through
me. "That was all your doing. You are one hot little Babe, Dennis or
should I say Denise. It suits you better." I sat up pulling him to me
and kissed him stuffing my tongue down his throat. Breaking the kiss I
said "This is going to be interesting, Best buddy, This is going to be
interesting."