Charles in Charge
- 4 years ago
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Charles In Charge free porn video
Part I
There were many times when I thought about doing it, but tonight was
the night I was to embrace my opportunity...
First let me tell you a little about me! I'm 23 and I go to grad school
in Chicago. I live alone, in the "boystown" area of Chicago, but to the
outside world, I've never been confused as anything but straight.
However, when the lights turn low and the late hours creep up, I'm
often checking out local personals sites, topics sights, and erotica
online, masturbating to my fantasies. Occasionally, I'll interact with
a few people, but for the most part I tend to shy away from actually
meeting these people.
Then I met Charles...
I met Charles through a posting I had on a local "meat market"
personals site, indicating the following: Grad Student, Masculine, 6'3,
190, white, preppie, short brown hair, green eyes, relatively beginner,
6 inch cock, good looking, muscular, discreet, seeks Alpha Male Top.
Tall, Rich, Dominant, Masculine, jacked to use me as they like. NSA or
fucktoy at your pleasure. Send Pic for Pic. Anal virgin here but
magnificent cocksucker... I live alone and can host...
Charles came across as very cocky, exactly what I was looking for. His
first email he sent to me included nothing but a picture. No words, not
even a subject, just a picture. But his picture got the point across...
He was a tall (6') and in shape, masculine, a little older (37). He had
these fabulous washboard abs that I know he put a lot of work into, and
he was cut! Rigid pecs, sculpted arms and bulky shoulders! He said he
worked out daily, and I believed him! He had a rather large penis too,
8 inches long and 6 around! He seemed to be everything I was looking
for. He worked in sales, and had the salesman personality. Not the
desperate used car salesman, but the high-powered corporate salesman
type... Witty, bright, optimistic, pleasant! The best part? He had a
very striking similarity to Pierce Brosnan, of James Bond fame!
Hearththrob!
Charles had not one, but two girlfriends already! I was wondering when
he could find time for me, and part of me liked the fact that I would
be his personal whore to call when he was low... I just had to bridge
his bisexual tendencies with my crossdressing fantasies.
I had been a novice at crossdressing, but it gnawed at my curiosity. I
read erotica on it all the time, and I even had tried on my mother's
lingerie a long time ago, testing out her makeup. I was a little too
tall to be passable, but I had the body for it. Small unimposing penis,
tight firm but not overly muscular figure, narrow shoulders, small
wrists and soft smooth skin. I couldn't grow much body hair, and liked
it that way. What I did grow below the eyebrows, I generally shaved
off.
I agreed to meet Charles at a local bar in a trendy north side
neighborhood. I picked him out of the crowd as soon as he stepped in,
and I could tell he was checking out the scenery more than he was
looking at me! What a tomcat! I walked over, dressed like the preppy I
acted like, and gave him a look in the eye and a firm handshake, the
both of us knowing inside I was melting! I had always been able to do
that, project masculinity when needed, but I always thought like a
schoolgirl internally.
We sat; he skipped dinner for drinks, me drinking a Cosmopolitan to his
Martini. I thought he would never stop talking about himself, and while
it was kind of a bore at the time, it was exactly what I was looking
for. He had attended a Big Ten school for undergrad and was now
attending a prestigious local university for his MBA. He had his own
office on the 37th floor of a tall Chicago building with a great view
of the lake that he wanted to show to me later! He laughed with a
reserved wit at the things I said, and I could tell he wanted to cut to
the chase. He told me that women were his passion, he could never fall
in love with a man, but he had a dirty desire within him to fuck
anything he saw, and cute men fit the bill. He told me he had two
girlfriends, one a lawyer who was all professional but turned into a
high school slut the second he smiled at her, the other a doctor who
was the classic lady but worked too much. He said one thing that
stuck... "All men need a good wife, a good girlfriend, and a good
whore". I could tell where I fit into the equation, and I liked it!
Now was the tough part, how do I introduce to him my sissy fantasies?
We were in a public place; I was scared people would overhear us. More
importantly, I was scared how he would react!!! It was now or never!
Luckily, it went over well, and he even seemed turned on by it. We
agreed to meet the next night, a Saturday. His girlfriend was cooking
him dinner, and then he was meeting "the boys" for drinks, and he would
call me at 3AM and expect me over promptly. I was to be ready, both
physically and mentally...
Part II
A day and night full of studying... At 1AM, I began to draw the bath.
Steaming hot water, I had my towel wrapped around me, assuming I had
breasts to hold it up, and it was failing me. Reality was catching up
with my fantasy world... Regardless, I leaned into the pool of water,
and slowly settled into its warmth. John Coltrane was being blasted on
my CD player, and I had a glass of vodka to sooth my nerves. I sat in
the tub, washing the bubbles over my smooth skin, shaving any hair I
had left on my body. I had poured a bit of flowery bath oil into the
water, and I hoped I would be close enough to him that he would smell
it in the near future.
Arising from my bath, I toweled myself dry, and sat down for the big
performance that would culminate from my time spent practicing applying
my makeup. I applied powder generously, until my face was a smooth
dough color, adding rouge to redden my cheeks. I put a touch of mascara
on my already curled lids, and eyeliner to define them further. A
bluish hued eye shadow complimented the green of my eyes, and for the
piece de resistance, a velvety dark red lipstick to fill in the lines
my lip liner set to shape. My blonde wig with the hair bobbed around my
shoulders completed the look.
Next, I looked at the fabric I had laid out on my bed to scintillate my
man. I may have only been his whore, and may have only wanted to be his
whore, but damnit I was going to be the best 4am whore he had ever came
across...or on!
Black stockings held up by a black garter belt, panties on above them
in case he wanted to bend me over his favorite chair with the stockings
still on... A matching black bra to encase my breast forms, applied so
delicately and perfectly that he would have a hard time differentiating
them... I sipped my whiskey and appreciated the look in the mirror...
black silk contrasting upon my smooth creamy skin...
I looked at the black cocktail dress I had hung up in preparation... he
had bought it for me and had it delivered that same morning, and it
would hug every curve I had... When it was on, along with my 3" black
heels, I looked in the mirror, spinning around as the nylon and cloth
skirt swayed with the momentum, I was sexy! I sprinkled on some
perfume, and grabbed my purse, filled with sex oils, lipstick and my
keys, and I heard my cell phone ring...
"Hello?" who would be calling but him at this hour?
"Hi, are you ready?"
"I'm on my way"
That's all that was said, as I hit the lights and caught a cab. The
cabbie was a bit more talkative than usual, and when I paid him, I made
sure to give him a look he could remember as he worked the night
away...
I rang his doorbell. He answered with a grin, looking me up and down
like the piece of meat I had made myself out to be. He was expectant,
demanding and satisfied... for now. He invited me in, and handed me a
martini, with some soft jazz on in the background...
His condo was well decorated, and we sat on his leather couch...
Chatting briefly, I expected him to be a bit tipsier than I found him,
and I found that attempting to "catch up" while dressing might have
been a mistake. I was buzzed...
Immediately, he set my drink aside, and grabbed my waist with his
available hand. His lips met mine with a deep powerful kiss. Used to
playing the male part in this game, I was not used to having a tongue
shoved down my throat, but I enjoyed his exploration. He was fondling
me intensely when all of a sudden, I was in the air! He had picked me
up and carried me into his private room, decorated with candles along
the walls and a black comforter covering a full sized bed. He
delicately placed me on the bed, and then removed his shirt! Wow, even
better in person!
As he climbed on top of me, he began lifting the dress above my waist,
and I felt the pinnacle of femininity. I was looking for someone to
make me melt, and he was doing just that!
In no time, my dress was on the floor and I lied there in my bra and
panties, him with his shirt off. I climbed on top of him, resting my
ass on his crotch, letting his object poke at its eventual target. I
slowly removed my bra, leaving me in just my panties, stockings and
garter. I climbed down to his belt buckle, and removed it with my
teeth, all the while using my palm to massage the hard object
protruding from beneath. I unzipped his fly, and that object of desire
whipped out to my surprise. It was hard, imposing and it made me drool
in delight. I licked the head, and it started jerking a bit under my
control. I had turned him on!
I then began to lick and savor the penis head, sliding my tongue to the
underside of his hole, with my thumb massaging the underside of his
shaft, where I knew I would want to be touched if I was him. His
breathing was intense and his groans were hidden between breaths. As I
sucked on his head and massaged his underside, he began to flex his
waist and fuck my mouth! I was just a face for him to fuck; I was just
his little slut. He began to breathe heavier and heavier, as I began to
see the room spinning... Had he spiked my drink? It was a fantastic
feeling, a feeling of utter submission to whatever he wanted me to do.
I seemed sober, to myself and my thoughts, but my body was under his
command! All of the sudden, the blow job began to be too much for him,
and he started groaning and removing his cock from my mouth.
"Get on your stomach, now! Face down, ass up bitch!" he yelled at me
forcefully. I wasn't going to disagree, and acted accordingly. In
addition, I spread my legs open wide, knowing that if that wasn't a
command, it would soon be! Immediately, he jumped on my behind, his
hands spreading my panties until they seemed stretched beyond their
limit, and then... He had ripped them off! I glared at my panties,
split in half on the side of the bed, as I felt a sudden member press
against my rosebud. I had lubricated it in the bathtub, but I had hoped
he had planned on using a little more, I liked the slip and slide
feeling...
Wow! So that's what it feels like with a dick inside of you! He began
fucking me, not just thrusting into me, but fucking me! He had applied
some sort of lube to himself, and it was slipping in and out easily. I
curved my body to take him in as far as possible, and as he went deep,
I pushed my waist in, as he pulled out, I pushed my waist into the bed.
He held my hands above my head, rendering my useless and out of control
to the object invading me, and he fucked me mercilessly. The drugs,
whatever they were, were taking effect on me, flashes came her and
there, him kissing the rear of my neck as he buried himself in me deep,
the burn on my ass as he spanked me, and his hand lifting up my waist
to bury himself in me further the next moment. It was erotic, I was his
bitch. He started grunting and breathing heavily, it was coming soon!
He was going to cum inside of me...
And then it happened. Just when I thought nothing more could fit inside
of me, he spilled himself into my rear. The penetration became more
sloppy, he became more out of control of his actions, his grunting was
louder, and his hands dug into my chest. He actually bit my shoulder,
he was agonizing and impaling himself into me so good. I could feel the
warm gelatinous feeling of his cum inside of me, and he pulled himself
out. He rolled me over, and I thought he was about to kiss me, when he
moved up and stuck his penis in my mouth, and I sucked the remaining
cum out of him and off of him. I felt so complete!
What a wonderful high feeling... I had asked him what he drugged me
with, and he said nothing, I must be high off of his fucking me...
We settled down, our heartbeats slowed, and we lied there on his bed...
exasperated.
The phone rang. Who would be calling at 4:30am??? He answered, talked a
bit, and then looked at me with a stone, imposing face:
GET OUT!
Lianne
- 23.09.2022
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