Cassies Close Shave
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Cassie's Dream Date 6 (the Final Installment) free porn video
This is the sixth chapter of Cassie's Dream Date. In the first chapter,
Cassandra (Cassie) meets Roger Wilson, author of "Love, Lies, and Lust,"
a story of transgender love. She's 30, and he's 40-something. She's a
supermodel. He's average, dresses well, and has a nice car. They make a
date to have dinner and go dancing later. Cassie gets his phone number
written on her hand. After he leaves, she has a wild fantasy date, which
turns out to be pure fantasy, as she had been daydreaming the whole thing
in Starbucks. In the second chapter, she gets ready for her date by
masterbating onto his picture. He arrives at her house. They go down to
his Ferrari. Cassie has a wild fantasy about him giving her a helping
hand while he drives, and finds that Roger hasn't even gotten into the
car yet. In the third chapter, Cassie fantasizes about having sex with
Roger in her living room. She leaves Roger, who peeked at her streaking
through her apartment wearing only her shoes and earrings, in a leather
bondage hood, so he wouldn't peek. After he had been in the hood for a
while, Cassie asked him if he was a sub, to which he answered yes. After
giving him a lap dance, she promised him a special reward for maintaining
his erection for 30 minutes. After 30 minutes, he was still hard, so she
allowed Roger to give her a blowjob. At the end of the blowjob, Roger was
given the opportunity to relieve himself, but surprised Cassie by just
getting dressed. In chaper 5, Cassie and Roger exchange witty banter and
Roger's background over dinner, and then go to Roger's McMansion to watch
a game in his media room with it's 102" screen and fully accessorized
seating. They both fell asleep after the big meal. Cassie had a dream of
fabulous sex with Roger, but alas, only a dream.
Chapter 6: The final chapter
And then I woke up, still sitting in the media room snuggled under
Roger's arm, the game in the second quarter, Roger was sound asleep.
I laid there I listened to Roger's breathing. He was in a deep sleep.
And I was very horny from my last dream! My Latina wonder was literally
throbbing in my panties, aching to be un-tucked. My sphincter was,
likewise, looking for some attention.
I wonder if Roger would mind being woken up so I can get some proper
relief?
No, that would be impolite. He's obviously wiped out. I should let him
sleep.
I need a drink. My throat is kind of dry. There's a refrigerator at the
back of the room. I saw it when we came in. Knowing Roger, it's probably
stocked, as well.
Carefully, I removed the remote control from his lap. The remote had a
big LCD display. When Roger used it last, he showed me that the "buttons"
are touch spots on the screen. It was showing a diagram of the room, with
two chairs lit up in blue. They appeared to be the love seat we were in.
I touched the spot that had my side of the love seat, and a number of
buttons appeared. I touched the button labelled "Un-recline" and the seat
moved slightly more upright. I touched it again. It move slightly more
upright. I put my finger on it and held it. It came fully upright.
Roger was still sound asleep. I gently got up, taking the remote control
with me.
When I got to the back of the room, I opened the refigerator and found
Champagne, beer, white wine, a variety of soda, and some bottled water. I
chose the bottled water. Next to the refrigerator was a cabinet of
glassware, so I chose a suitable glass.
Tucking the remote under my arm, I went back to the front of the room to
watch some more of the game. I chose a chair a few away from sleeping
Roger, so as not to disturb him.
After a bit of a very boring and lopsided game, I decided to look at the
remote, which fascinated me. As I touched each chair, the standard menu
came up for recline, massage, and heat/cool, until I reached the "special
chair". When I got to that one, it had another choice, "Play".
I touched the "Play" button. The image on the screen was replaced with a
side view of the chair, which included the dildo, and a number of
buttons, "Rotate Faster,""Rotate Slower,""Rotate Stop," "Up," "Down,"
"Thrust Faster," "Thrust Slower," "Thrust Stop," "Rock Wider," "Rock
Narrower," "Rock Stop," "Lube," "Restraints On," "Restraints Off," and an
enigmatic one called "Orgasm".
I pushed the button that said "Up," and the screen showed the dildo go up
a little bit. I pushed the button that said "Down," and the screen showed
the dildo move down. I looked over at the chair with the pillow on it,
then pressed and held the "Up" button. I could see the pillow move. This
IS very cool. I pressed and held "Down" until the dildo on the screen was
all the way down.
I pressed and held the "Rock Wider" button for a couple of seconds, and
the screen showed the dildo moving front to back. The pillow was being
moved as well. I pushed "Rock Stop," and the motion stopped.
My sphincter began that familiar itch, as I was getting excited playing
with this marvel of engineering.
I pushed and held the "Thrust Faster" button, and the pillow flew off the
chair, revealing the dildo rythmically thrusting up and down. I went over
for a closer look.
It was moving kind of fast, like a young man getting his first piece of
tranny ass. I pressed "Thrust Slower" and the up and down slowed to a
reasonable fucking speed. Wondering, I pressed the "Rock Wider" button.
The dildo began to thrust and move back and forth. Watching it move like
that mesmirized me. My Latina wonder was throbbing hard in my panties. My
sphincter was seriously wanting something hard.
Roger was still sound asleep.
I pressed "Rock Stop" and "Thrust Stop," and the dildo came back to its
straight up rest position. I pressed "Lube," and a white liquid dribbled
out the head of the dildo. It looked like come.
Roger was still sound asleep.
My sphincter was aching. My Latina wonder was aching. I was wearing a
dress.
"Fuck it!" I said to myself, as I removed the offending panties. The
Latina wonder tent-poled my dress. I reached underneath and gave it a
little massage, while looking at the dildo sitting there with what looked
like come dripping off the head. I reached out and touched it. It was
quite greasy. I spread what little got on my finger onto my rosebud, and
then dipped the finger in.
It didn't take me long to realize that my finger would be insufficient to
satiate the need my ass felt.
Roger was still sound asleep.
Hiking up my dress, I lowered my ass down until it came in contact with
the dildo. I pressed "Lube" again, and was instantly rewarded with a wet
rosebud.
I eased myself down. The dildo wasn't very thick, but it was a good size
for me. Eventually, my thighs landed on the leather of the chair base
itself. When my full weight was down, the dildo was all the way in.
I carefully and lightly pressed "Thrust Faster," to be rewarded with a
very slow in and out movement of the dildo. It felt great!
I carefully and lightly pressed "Rock Wider," and the dildo began a
forward and backward dance. I pressed it again a few seconds later,
giving it more movement, and it was now driving my ass wild. My Latina
wonder dribbled pre-come onto my hand, which was stroking it with gusto.
I looked over at Roger. He was still sound asleep.
Throwing caution to the wind, I pressed the "Orgasm" button. The dildo
stopped, and the remote let out a long beep. I looked at it, and it said
"Chest/Lap Restraint" in blinking red letters.
"Ok," I thought. I pulled on the seat belts. One across my thighs. The
one under my breasts required me to hike up my dress, so I just took it
off. If Roger woke up and saw my naked breasts, it wouldn't be the first
time.
I pressed the "Chest/Lap Restraint" red button, and heard a click. The
"Chest/Lap Restraint" in blinking red letters disappeared. The remote let
out another long beep. This time it said "Wrist Restraints" in blinking
red letters.
I thought that was a bit much, so I pushed "Orgasm" again to hopefully
cancel it, but it just kept beeping and saying "Wrist Restraints" in
blinking red letters.
I flipped open the arm rests, revealing the restraints Roger showed me
earlier. I pressed "Wrist Restraints," but nothing happened. The remote
just kept beeping and saying "Wrist Restraints" in blinking red letters.
Roger was still sound asleep. How much longer with this beeping, I don't
know, however.
I put the remote control on my knees, and slipped my left arm into the
sleeve that was the wrist restraint. I pressed the "Wrist Restraints"
button, but nothing happened. The remote just kept beeping and saying
"Wrist Restraints" in blinking red letters.
Realizing this needed both hands, I took the water bottle and slipped it
into the right wrist restraint. I pressed the "Wrist Restraints" button
and the sleeve holding my left arm tightened, holding my arm to the
chair. The right restraint was holding the water bottle tightly.
The remote control stopped beeping, and put the word "Calibrating" on the
screen.
I felt the dildo began to slowly move fore and aft. And then it stopped.
It moved out a little, and did it again. It then seemed to rotate, and it
did it again. My ass was thoroughly enjoying the attention. My Latina
wonder, caught between my thighs, was aching. And then, the movement
stopped.
I looked at the remote control. It said "Excessive movement! Restart?". I
felt suddenly foolish, as my ass was so enjoying the attention that I had
started to samba in the chair, wiggling my ass quite a bit. I pressed the
"Restart" button, was rewarded with "Calibrating" and a pleasurable
movement of the dildo. I was trying my best to stay still. And then, the
movement stopped again.
I looked at the remote control. It said "Recline?". I pushed it with my
free right hand. The chair reclined. Pretty soon, I was laying out, with
my Latina wonder pointing at the sky and my knees slightly elevated. My
breasts, wonders of silicone, pointed at the ceiling.
I felt the dildo began to move again. I held up the screen to see what it
said. It was back to "Calibrating".
The movement of the dildo was amazing. It must have figured out where my
prostate was, because it was causing me to shoot come every 30 seconds,
almost as if it was timing it, by thrusting or rotating the head of the
dildo across my prostate at just the right angle.
I looked over, my vision a haze due to the pleasure in my ass. Roger was
still sleeping.
The dildo stopped. I held up the remote control. On the screen in red
letters was "Orgasm!".
A second later, the dildo began to pummel my ass, thrusting fast and
retreating slow, rocking back and forth, and rotating so I could feel all
the sides of the dildo's head. I felt more lube. I dropped the remote
control onto my knees, and grabbed my Latina wonder.
My breasts bounced. My Latina wonder was covered in come and in need of
relief. My ass was in nirvana, the rubber miracle of engineering
attenting to every need it had, and more.
I stroked the Latina wonder as the dildo began to slow. As it neared a
full stop, it began another pattern of thrusting and rotating and rocking
even better than the first, gaining speed as it went.
I came. The Latina wonder shot come so high I expected it hit the
ceiling! The dildo continued its unrelenting assault on my ass, which
was loving every moment of it.
I glanced over at Roger. Still asleep! How could he sleep through this!?!
The dildo wasn't stopping. I felt more lube in my ass. With my come
covered hand, I picked up the remote to see what it said. On the screen
was a yellow "Orgasm" message. I took that as a good sigh, especially
when the dildo began to slow. The remote fell out of my slick-with-come
hand and onto the ground.
Suddenly, the dildo got wider. Thicker. It was getting larger. I could
feel my sphincter stretching to accomodate its new girth. It felt like I
was giving birth. My sphincter was now in pain. I tried to get off, but
the seat belt was holding me down.
I pushed the button on the seat belt, but it didn't release. I could feel
more lube in my ass. The dildo grew slightly smaller. The lube ran out my
ass. The dildo began to rotate. My sphincter wasn't use to this size, and
felt stretched to its limit. After a few moments, the rotation stopped.
The dildo slightly shrank again, and then began to move in and out.
The new found size of the dildo was causing every stroke to run the edge
of the head over my prostate. My Latina wonder was now soft, but
literally pouring come onto my thighs and the leather seating surface.
The strokes got deeper. I was being lifted off the chair, slightly, with
every inward stroke. I held on to the arm rests with both hands. The ride
was getting rough. My ass was on fire with the big dildo probing every
inch of my entire colon.
I closed my eyes and began to really enjoy the ride, imagining it to be
Roger pounding my ass instead of a rubber monster.
I came again. I wasn't hard. I wasn't stroking the Latina wonder with my
hand, but still I came. My body seemed to lift off into space. I was
there for a whole minute, a dildo filled nirvana. I may have screamed. My
ass gripped it so tightly, I could tell it slowed down, and not because
it wanted to.
As I came down from the most intense orgasm of my life, I realized I was
suddenly chilled. My sweat covered body was in a 65 degree room. I
breathed deeply, still out of breath from the orgasm. The dildo was still
in my ass, but, thankfully, not moving.
After a minute or two, I felt a warm touch on my left breast. I opened my
eyes. Roger was very lightly wiping the sweat off my nipple, with his
tongue.
I smiled. It was fairly erotic to be laying here, post orgasm, naked, in
a strange man's house, and having him licking your breasts.
When he was done with his task, he looked up at me and smiled.
Exhausted, I gave him a little smile.
He stood up, and went to the other side of the chair. Kneeling next to
it, he began to lick the sweat off the right nipple. I wiggled a bit,
making him work to keep it in range of his tongue. My only free hand
touched his chest.
Satisfied he had finished up, Roger stood up, holding the remote in his
hand. His hand danced over the surface as he looked at it intently.
"You need to put both hands into the restraints. It's the way the chair
is designed." he said
"I was afraid." I said
"The chair has sensors in the arm restraints that sense your pulse and
blood pressure. The chest restraint measures respiration, as well. I
guess you figured out the dildo itself has sensors to find out if you're
enjoying what it's doing. If the chair sensed you were in distress, it
would have automatically stopped." Roger said
"Oh..." was all I could say, as I felt the dildo move a little.
"The chair stopped before going to 'ultimate orgasm' because it couldn't
calculate your blood pressure because you have a water bottle in the
restraint instead of your arm." he informed me.
"What I just had WAS the ultimate orgasm." I sighed, as the dildo moved
yet again.
"Trust me. It wasn't. " he said
"The dildo is still moving around. Why is it doing that?" I asked, as the
dildo rotated inside me.
"It's waiting for you to reach a relaxed state to start the next phase.
While it's waiting, it moves the dildo around so that your ass stays
evenly lubricated." he said
"I don't think I can take any more." I said with a sigh.
"The chair was designed to not allow the occupant to leave until they've
reached the ultimate orgasm phase. Sorry, that's just the way the ex
designed the Orgasm program. I've tried to figure out ways to override it
myself, but haven't found any." he informed me.
"What?!?" I said, the dildo moving yet again.
"Seriously, you'll have to have at least another orgasm before it will
let you out. And then, maybe not even then, if it doesn't think it's big
enough." he said
"What??!!!!!" I cried "I can't go again!"
"Don't get worked up. I'll be right here." he said
I began to cry. I felt him take my hand.
"If you put your right arm into the restraint, it will probably let you
go after the next orgasm." he said.
He pulled out the water bottle, not an easy task, and I allowed him to
put my arm into the restraint, which tightened immediately.
I heard a beep and looked at Roger. He was staring at the remote.
"What's wrong?!" I asked
"It's about to start again." he said
"Oh..." I said, as the dildo slightly deflated and began to thrust,
rotate, and rock in my ass. I was now beyond words. I could feel lube
dripping out of my ass. I felt a hand on the Latina wonder, pulling it
out from between my thighs where it had fallen after the last orgasm.
Trust Roger to lend a helping hand. I smiled at him. He didn't let go.
As promised, the chair gave me an orgasm like I never had before. Roger
sat there next to me, holding my Latina wonder as I nearly lost
consciousness, floating away on a cloud of bliss, the dildo chair my new
best friend. I'm sure I screamed when I had "the ultimate orgasm".
As I laid there catching my breath, the chair released the wrist
restraints, and Roger unbuckled the thigh and chest restraints.
"The chair controller says you achieved Ultimate Orgasm in only 28
minutes. Three orgasms in 28 minutes! You're like a 16 year old!" Roger
informed me
"It felt like an hour, and only a minute, when you're in the chair." I
said
"How true..." he sighed
When he thought I was ready, he un-reclined the chair, and helped me off
the now deflated dildo. From somewhere unseen, he handed me a towel to
put between my legs, as they were literally covered in white lube, my
come, and sweat. My sphincter hung open. The Latina wonder was in a
shrunken state, with no stirring whatsoever as Roger used another towel
to dry it.
I began to cry.
"What's wrong?" he asked
"This is not what I wanted for my first date with you. I look like a pig
now, and I'm sure I smell like one, too!" I cried
Roger stood up and hugged me. "You're incredibly beautiful, but you do
need a bath." he said, warmly and with a little giggle.
I slapped his back. "So, where's the bath?" I said with a whimper.
"Can you walk, or are your legs jello?" he said
"Jello." I said, still holding onto him tightly.
"I'll carry you, then" he said, slightly stepping back and putting his
hand underneath my ass. He had me in his arms a moment later.
"Don't you need to clean up the chair?" I asked, as he held me there.
"I have a maid. And, besides, the chair was made for that, so nothing we
do to it will stain it permanently. It'll keep until Mona comes in
tomorrow morning." he boasted
I held on as he carried me through his house, up the stairs, and into a
beautiful master bedroom and then into the bathroom. He sat me down on
the counter, and gave me a kiss when he was done.
He turned to put the water on in the jacuzzi tub.
"Roger" I said
"Yes?" he said
"There are things a girl needs to do in private after being fucked to
three orgasms. Can I have a little privacy for a few minutes?" I said
"Of course. Yell if you need anything." he said, as he left the room,
closing the door behind him. A perfect gentleman!
I hopped off the counter and made a bee-line for the toilet. The towel,
which had sopped up most of the lube, fell to the floor as I made my
dash. No sooner did my ass hit the seat than I felt what must have been a
whole cup of lube pour out of my ass. While waiting to see if there was
more coming, I looked over the towel. I was sure there would be blood,
but not a single drop was on it. When I wiped a few minutes later, it
too, was blood free.
I carefully wiped myself, to get any lube or other unmentionables off of
me before I flushed. Surprisingly, my ass was only a tiny bit sore, like
I had used my thinnest dildo. I guess the white lube was the key, because
that machine really fucked me good!
I checked the water temperature. It was perfect, and the tub about half
full. There were some bath salts on the counter, so I threw a handful in.
The bath smelled nice and it began to foam. My lower body ached. My arms
ached. Even my breasts ached from bouncing. I lowerd myself into the
water. The warm water enveloped me. I turned on the jets. The foam began
to rise. It was wonderful.
"Roger!" I yelled
A moment later, Roger slightly opened the door. "Yes?" he said, through
the crack
"You can come in now." I said
He opened the door and saw me in the bath, covered in bubbles. "Wow!"
"Come on over." I said, in my best seductress voice. As he came closer, I
reached out a hand.
He took it. I grabbed on to his hand and pulled him towards the water.
"Join me" I said.
"Ok, let me get my clothes off." he said
"Do it quick" I said
He was out of his clothes in less than a minute. His hard cock bobbed as
he climbed into the tub with me. The water, still on, began overflowing.
Saying nothing, he turned off the water.
We came together in the middle of the big jacuzzi tub, for a beautiful
kiss.
When we broke the kiss, I said "Roger, you'll fuck my ass later tonight,
right?"
"Yes, darling." he said
"And you'll do it all night, right?" I asked
"Yes, if you can take it." he said, with a smile.
"Oh, I can take it...." I said, giving him a huge kiss and laying down
over him.
We washed up. Or, more precisely, he washed me. With his hands. Slowly.
Sensuously. He didn't miss a spot, either.
By the time we were dry, the Latina wonder was achingly hard again. He
offered, and I accepted, relief.
His oral skills were beyond reproach. Without the mask, I could see his
face light up in delight as he sucked on the Latina wonder, and the sheer
joy he received in my gift of an orgasm. Even though what came out was
probably miniscule, he treated my come as a fine offering of the best
beverage in the world.
When he took me to bed, he was a slow and patient lover. His cock, every
stiff, was just the right size for my hole. I enjoyed every hour of our
lovemaking.
When I saw the sunrise through the window, I told him it was dawn and he
could come if he liked. He delighted me by pulling out of my ass and
coming on my breasts, which has always been a fetish of mine. I like the
sight of come dripping from them. It validates what it means to be female
for me, knowing that I can extract man love juice, and that they desire
me.
We slept for hours intertwined on the bed, awakened only when his maid
came in to clean that afternoon. She was black, 300 pounds if she was an
ounce, and about 60 years old. So much for my daydream of a pretty
ladyboy maid!
I told Roger about the ladyboy daydream. He laughed, thinking it made him
sound way too sinister.
When we finally got up, the maid had brought my dress, which she had
ironed, and my panties, which had been freshly laundered, and had placed
them in Roger's dressing room.
After I got dressed, I looked into the closets in the dressing room.
Inside one large closet was the most beautiful white gown I had ever
seen. It looked to be my size, as well. I brought it out to Roger.
"Roger, this is gorgeous! Who designed it?" I asked
"A local fashion student. She did it for a class project." he said
"It's not your size, so whose is it?" I asked
"No ones. I was asked to be a judge at a competition among various young
designers. When I saw it, I thought it was beautiful. After the contest
was over, and she won with the dress, I offered to buy it. It was rather
expensive, even though it was from a no-name designer, but I had to have
it because it was so nice." he said
"It looks to be my size? I guess she had a fashion model in mind when she
made it!" I said, somewhat boastfully.
"I'd say if it fits you, you can have it, but it would be bad luck for me
to see you in it." he said, quizzically
"Why bad luck?" I asked
"Because it was designed to be a modern wedding gown." he said
I laid it across the bed. Yes, it kind of looked like a wedding gown.
"I'm trying it on!" I said, as I grabbed it up and ran back into the
dressing room.
It didn't take me very long to see that the gown WAS my size, but it was
a little tight in the top. My breasts were popping out the top. Most
fashion models are rather flat chested, unlike me. "Roger, it's really
close to my size! It's just a little tight in the boobs!" I yelled.
"Great! Don't come out with it on. Bad luck!" he yelled back.
I took off the gown and put my own dress back on. I hung up the gown and
came out into the bedroom.
"Where's the gown? Don't you want it?" he asked
"It's in the closet. Of course I want it, but I want you more!" I said
with a growl, pulling him into a long kiss.
As we broke the kiss, he whispered into my ear "Do you like jewelry?
Rings? Diamond rings?"
I squealed "Yes! Yes! Yes! I do! I do!"
"Come with me" he said, taking me by the hand to his dressing room.
There, he stood in front of a mirror, pressed the edge, and revealed a
wall safe. He opened the safe, fumbled around in it, then suddenly knelt
down and produced a ring box, which he opened to show a HUGE diamond
ring. "Will you..." he began
"Yes!" I cried, knowing Roger is the man for me.
"...wear this in your nose?" he said
"No!" I said, pulling away laughing
"Ok, how about just marrying me and making me the happiest man on Earth?"
he said
"Yes!" I said, holding out my left hand.
The ring was sized a little too large, but we took care of that quickly
enough. The next day, we flew on a private jet to New Hampshire, where we
set up residence in his vacation home, changed our driver's licenses and
voter registration, and got a marriage license. We found a seamstress in
the local town to let out the chest on the gown the same day.
Eight days after our first date, I became Mrs. Cassandra Wilson in the
gorgeous gown! I was stunningly beautiful on my wedding day. My friends
from the fashion industry were agog at how an unknown college student
could make such a dress as a class project. A local papparazzi got
pictures of my in the gown with some of my designer friends. When they
were published, the subtitle was "Which one designed the dress?"
Roger's assistant worked magic and got all of my relatives and many of my
friends there. Roger's friends and relatives also made it. We had every
limousine, rental car, hotel, and bed and breakfast in the county engaged
for the event. The catering was done by his chef, who flew a planeload of
food up from the restaurant, along with his sous chef and all the
waiters. We took over the largest restaurant in town for the reception.
The day was entirely magical for everyone involved.
That evening, after we got back to OUR home, I gave Roger one of his
choicest fantasies... Removing the wedding gown on his new wife,
revealing a large, dark, and very suckable cock, already dripping in
anticipation of her new husband's expert oral skills, and getting the
creamy reward he deserves for marrying her.
Roger's fantasy was lived out several times that night. He had me put the
gown back on so he could take off the gown each time. Since then, I've
worn the gown many times, often to social events, with Roger always eager
to leave early...
I tracked down the young designer, and introduced her to people I knew in
the industry. She's now "on her way," and I'm her biggest customer.
I pinch myself often, just to make sure it's all been real. So far, it
has.
If you liked this story, feel free to email me and tell me! Only through
feedback do I know that people are reading!
George Wilson
[email protected]
Emely
- 16.12.2022
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