Winter Break
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Winter Break Part II free porn video
WINTER BREAK PART II
BY CCNC
Twenty minutes later Mike and I were loaded into
his SUV and on the road for the 3-hour drive to
the beach. Neither one of us had said much since
I finished my "show." Finally, shaking his head,
Mike said "I can't believe you are a crossdresser.
I mean there have definitely been stranger things
that came out of California than a guy like me that
likes to wear women's clothes. But, you! - Mr.
Straight-laced Southern Boy! ??.How did you get
started?"
So I told him how it really started about 4 years
earlier (I was 15 at the time) mostly by accident
and out of boredom. My sister had just moved to
college in the Northeast and my mom and dad were
gone a lot. I didn't drive yet, so I spent a lot
of time around the house in the evenings by myself.
Being the horny teenager I was I looked for anything
to get me off. One night I was watching TV when
someone on a sitcom had to wear women's clothes. For
some reason it hit me as an interesting prospect. Ten
minutes later I was rummaging through my sister's
closet and drawers.
For a while it was just panties or a slip to jack off
with. Then I started wearing panties under my jeans
to school on days I didn't have gym or sports practice.
By the time college rolled around, I could drive and
had put together my little wardrobe and started
dressing fully when my parents were out of town for
the weekends. During this time I was able to find
more and more information on the Internet - both
sexual and non-sexual. It seemed to me that a lot
of heterosexual guys liked to dress up. With that
information in hand I rationalized my "hobby" as not
so weird and just enjoyed myself. Until half an hour
ago, I had never ever thought about sex with a guy!
Mike seemed to be taking it all in. Finally I said,
"So do you dress completely or just like wearing sexy
stuff under your regular clothes? By the way, those
are some sexy panties you have on."
Mike kinda of laughed and said "believe it or not, I
can remember wearing my mom's clothes as young as Seven
years old. Who knows were it came from, but that's
the fact."
He went on to tell how as he got older it became clear
it was not exactly normal behavior, but he couldn't
make himself stop. He'd steal a pair of underwear
every once in awhile from the hamper. When his parents
were gone and the nanny stayed with him, he would sneak
into his mom's closet and grab stuff to try on. In
high school he kept it well hidden. With his allowance
and the fact he got a car at sixteen, he had total
freedom to shop and buy stuff. The Internet was a
big deal to him too, but he seemed more into the sexual
aspect of dressing up. He admitted that he really did
like triathlons and the training kept him in great
shape, but it was also a good excuse to shave his body.
We continued talking about how and why and what we had
done over the years to fulfill our desire to dress
and the lengths we went to keep it a secret. Before
too long we were almost to the beach. Mike pulled
into a convenience shop and came out with a six-pack
of beer. "This is for the last 45 minutes of the
ride" He said. "Just to start the weekend right."
After we each popped a top, Mike said "Well, let me
fill you in on what my usual weekends away are like.
To be honest, I use the time to dress up completely
and usually for the entire weekend. I work it out
so I arrive at night. I go in and unpack and then
start my transformation.
When we get in, I'll take a hot show and shave. Get
my wig styled and put it on. Slip into panties and
a nightgown. And then sit on the couch with a glass
of wine and paint my finger and toe nails. Since
I now have company, you can join me. It'll be fun.
We can have what my mom use to call a "princess
evening!"
Wow. Mike was really into this. I was very excited,
but sort of freaked out too. Mike's demeanor had
completely changed. He was almost giddy with
excitement as we got closer to the beach. I had
never seen him like that before. Normally, he was
Mr. Cool and very laid back.
Finally, we pulled off the main highway and pulled
up to the main gate for the gated beachfront community.
The drive from the gate to the house took another 10
minutes. We drove by the golf course and clubhouse,
the tennis facility, the marina and a ton of huge
homes. Even at night you could tell this was a really
nice place. It was definitely off-season (being
February) because most of the homes were dark. It
looked like Mike and I would have the place to
ourselves - total privacy.
When Mike pulled into the driveway, I thought he was
kidding. The house was huge and right on the ocean.
Mike reached up and hit the built-in button in his
SUV and the garage door started to open - I guess
he wasn't kidding after all.
The house was fantastic and beautifully decorated.
The ground floor was a 3-car garage with storage
and had the laundry room and pantry. You could
take the steps upstairs or ride a small elevator.
The first floor was stunning. The living room/den
was sunken and had an entire wall of glass facing
the ocean. The kitchen and dining room were to the
left. The master bedroom was off to the right. The
kitchen had every thing any cook could want and then
some. Gourmet didn't even come close to describing it.
The master bedroom was huge with a king-size bed and
small sitting area with its own TV. The bathroom
was done in off-white marble and had a separate
tub/Jacuzzi and shower.
I followed Mike into the master bedroom where he
tossed his stuff on the bed. He then gave me a
tour of the rest of the house and showed me my
bedroom. The top floor had four bedrooms - each
with its own bath. I took a room on the front so
I would have an ocean view. The room had a queen
size bed, dresser, night tables and a nice chair
and ottoman.
Once I was shown my room, Mike said, "I'm going to
get a shower and get changed. Come on down when
you're ready. I'll open a bottle of wine and leave
it and a glass for you on the wet bar. Make yourself
at home. See you downstairs."
This was a great place and I was very excited about
spending an entire long weekend as Gena. The emotion
of getting caught combined with the 3-hour drive had
really wiped me out. I decided a shower was definitely
in order. As I turned on the shower and pulled an
expensive lush towel out of the linen closet, I made
up my mind to shave my legs tonight. Hell, this was
going to be a very special weekend and I wanted to go
all the way to look good.
Mike had been encouraging me the whole way down to
give it a try. After I had had a good soak in the
hot steaming shower, I lathered up my legs and went
to work. It wasn't as easy as I thought it would be
plus I had more hair than I realized. I started at
my ankles and worked my way up. The problem was
finding a place to stop. Before I knew it I had
shaved my legs, arms, chest, underarms and face!
I toweled off and found some nice smelling lotion
under the sink. My brown hair was short so it didn't
take long to dry. I wrapped the towel around me
and unpacked my stuff. I had a lot of stuff, just
not a lot of outfits: a couple of bras, several
pairs of panties, thigh highs with lace tops (black
white and suntan), 2 sexy little nightgowns, my 5"
black pumps and a pair of black heeled loafers, 2
mini skirts, 2 blouses, a sweater twin set (in pink)
and 2 short cocktail-like dresses (you guessed it
red and black). I also had my makeup and wig and
basic accessories.
I had also packed my running tights (really just
black cotton leggings I wore to run in when it was
cold), my running shoes and what I had worn down
on the trip - jeans, t-shirt and fleece pullover.
Since Mike, or I guess Michelle for the weekend,
planned to just lounge around on the couch tonight,
I slipped into a cute pair of high cut ivory panties
with a full stain back and a matching Ivory nightgown.
It had thin little straps and lace brocade on the top.
The feeling of silk against my now shaven body made
me shiver with excitement. I could hardly concentrate
on my wig and makeup.
My wig was brown like my hair and since my hair was
short, the wig looked completly real. Just for fun
I pulled my hair back into a ponytail. Once again,
I only used a light application of powder and lipstick
on my face. I did do my eyelashes with mascara and
liner. I clipped on my small hoop earrings, hooked
my anklet around my bare leg and sprayed myself with
a touch of perfume.
When I finally stepped back and looked at myself I
was shocked - there before me was not the usual
vision, but a real college coed - ponytail and all!
It was amazing what a difference shaving my body had
made. If I had had boobs and could hide my big
boner, I would have been totally convincing. I
didn't have a bra that would go with the ivory
nightgown so I had no boobs tonight. Otherwise,
I was more than pleased.
I skipped down the steps barefooted and felt my
ponytail bounce against my neck. Michelle was
already on the couch with her back to me. When
Mike turned around I nearly fainted for a second
time in 4 hours. She was absolutely stunning.
This was the first time I had seen Mike?. I mean
Michelle dressed up. She had blonde hair a little
longer than mine and her make up was expertly done.
She wore a short black nightgown trimmed in lace
with tiny straps like mine. But the thing that
completed the package was her breasts. I mean
she had what looked to be real boobs - erect
nipples and all. Her black nightgown draped
across them just right and her nipples protruded
a good quarter inch against the silk.
As Michelle stood and held out a glass of white
wine all I could say was "Wow, you look beautiful."
"Well thank you Gena, you look pretty good yourself"
she said. "What do you think of my tits? Pretty
cool, huh?"
"They're ?.perfect" I said. "How did you do it?"
"These are medical grade silicon breast forms,
attached with surgical adhesive, she said as she
cupped them and pushed the together. "I can wear
them all weekend without a bra if I want. I can
even get'em wet in the shower or hot tub!"
After I sat down and curled my feet under me on
the couch with my wine, Michelle walked over to
me and bent down a little. "Watch this," she said
and she shook her boobs in my face. "They jiggle
just like real ones, its such a great feeling"
She was right too, they did shake just like real
boobs. As she was bent over, I got a great look
down her nightgown. Her boobs not only shook like
real ones, but the color matched her skin. I
honestly couldn't tell they were fake!
"Want to touch'm?" she asked.
"Sure" I said and I gave her a good groping. My
mind was swirling again. They were completely
life-like. It was like Mike had grown real boobs.
It made me a little jealous as I sat there
flatchested and all.
With the boobs out of the way (literally), Michelle
and I sat on the couch and talked for a while. Had
anyone walked in, it would have looked like two very
cute college girls were having some girl time on the
couch. After a while we took turns painting each
other's toe nails and finger nails - drinking wine
the whole time.
I choose red to match my only lipstick. Michelle's
fingers and toes got a soft pink coating. Michelle
asked what I thought of my new hairless body.
"It feels great" I said. " I can't wait to roll a
pair of stocking up my legs."
"You'll probably cum in your panties when you do.
It's a very intense feeling the first time," Michelle
told me.
After two bottles of wine and the beers we split on
the way down, we were both a little tipsy and giggled
like, well, like schoolgirls. Michelle jumped up and
said "Oh my gosh, I almost forgot. Come with me, I
have a surprise for you"
She grabbed my hand and pulled me into her bedroom.
Michelle opened up a locked trunk in the closet and
started pulling stuff out. "This is my main stash of
stuff. I keep in locked in the back of the SUV," she
said. The trunk, along with the closet was full of
women's clothes and stuff. Finally she found what
she was looking for - a small white box.
I followed her into the bathroom as she took the top
off. Inside the box under the bright bathroom lights
were two breast forms.
"These are my old ones. They're 36C's. These babies
I'm wearing tonight are 38D's," she said. "I almost
forgot about them. How would you like some nice tits
for the weekend?"
I guess I didn't have to answer verbally because I
was too busy stripping my nightgown off. This was
going to be great. I was so excited and tipsy - I
wanted the total illusion. Michelle had me stand
in front of the mirror and hold my arms above my
head. Meanwhile, she sprayed adhesive on the breast
forms and then a little on my chest. Five minutes
later, I had beautiful perky boobs of my own.
I just stood topless in front of the mirror and
admired my now completely feminine form. The weight
of the breast forms pulling on my chest felt wonderful.
I reached up with my hands and cupped each of my boobs
and gave the nipples little squeeze. Michelle was
standing behind me and watching me in the mirror.
After a few moments, Michelle stepped up close behind me.
She ran her hands under my arms and around my chest so
she too could cup my new boobs. While giving my breasts
a squeeze from behind, I felt her silk nightgown against
my smooth bare back - it felt like fire. It as only a
brief squeeze/hug, but I was keenly aware of her rock
hard cock as it nestled between my ass cheeks. When
the hug was over, Michelle stepped back and said "Go
ahead, give them a good shake." Shake them I did, just
like a stripper.
My new boobs jiggled and bounced when I jumped in joy.
"Check this out," Michelle said as she led me into the
bedroom. "Get on the bed on all fours and see how they
hang down and pull against your chest"
On the bed I went and assumed the position. How many
times had I had some coed in this position as I fucked
her brains out from behind? It was always a bonus to
see a girl's boobs bouncing to the rhythm of your
thrusts. It was definitely a guy thing to see jiggling,
bouncing breasts.
Now I was experiencing the feeling. As I looked over
towards the wall, I saw myself in the mirror above the
dresser. I looked so sexy. Just as other crossdressers'
have said to themselves as the ultimate compliment, I
thought "I'd fuck me!"
As I watched myself, Michelle moved up behind me. Pulling
my ass into her groin, she slowly humped me from behind.
Bump, bump, bump. With each bump, my boobs swayed against
my chest.
"Doesn't it feel incredible to have tits?" she asked
in a dreamy voice. "I love the feeling of my tits
swaying while taking a nice big cock from behind."
Michelle was now in a world of her own - eyes shut,
humping and bumping away. I could again feel her
cock staining against her panties as it road up and
down against my panty-clad ass.
I was so horny and caught up in hte mood. I looked
so sexy in the mirror as did Michelle - two lesbian
lovers rubbing against one another. "Michelle,
please take me. Complete the transformation to Gena
tonight," I moaned. Let's face it - I had already
sucked a cock and swallowed cum today. I was dressed
up on a bed in the doggy-style position with my ass
up in the air. It only seemed logical - tonight I
was a women 100%.
Michelle, continuing to dry hump me, seemed to come
back to the present. A big smile spread across her
face. "Are you sure?"
"Just do it?.take my virgin ass and make it yours,"
I said all the time watching in the mirror.
Michelle jumped off the bed and returned with a tube
of something. She quickly pulled my panties down
around my thighs thereby exposing my smooth bare ass.
Suddenly I was penetrated by a wet, slick finger -
then two.
Michelle gently massaged my hole allowing me to relax.
As I pushed back against her hand, she reached around
and started stroking my hard cock. I was in heaven
with all the sensations running through my body. If
this is what getting fucked felt like, I was going to
love it!
"Are your ready sexy girl?," asked Michelle.
"Let me show you how ready I am," I said. Then I
reached back between my legs and grabbed Michelle's
cock and guided it to my waiting hole. Michelle
groaned in anticipation and, as if on cue, put a
hand on each ass cheek and spread me wide. I
positioned her cock head against my hole and gently
pushed back. Michelle's lubricated cock slide in
easily.
Suddenly the pain was so intense I thought I would
scream! This was not the feeling I had while she
fingered me - of course, Michelle's cock was huge!
Michelle must have sensed my pain. She stopped the
assault and told me to relax - the pain would go away.
After a minute or so, my breathing was back to normal
and I could relax a bit. Michelle then eased her
cock forward, caressing my ass the entire time. Before
too long Michelle was buried balls deep in my ass.
I knew I was about to split wide open, but the
fullness started to feel really good. S
lowly Michelle started to withdraw and then push back
into me. Soon she was withdrawing more and thrusting
harder in a steady rhythm. My boobs started to sway
and our breathing got louder. I watched the scene
unfold in the mirror - it was almost too much to see,
hear and feel!
After I relaxed and got into Michelle's rhythm, I was
thrusting back to meet her as she slammed into my ass.
Like the blowjob I had given earlier in the day, our
sex was loud and noisy, like animals. With every
ass-pounding slam, I could feel my boobs, ponytail
and cock sway forwards, then back. Michelle was
really fucking my brains out - I could feel her balls
slap against my bottom.
Suddenly, without warning, Michelle completely withdrew
from my ass. No, No I thought? don't stop! It was
then that Michelle slapped my ass with her hand and
said, " roll over!"
Now I was on my back, staring up into Michelle's face.
She took a pillow and put in under the small of my back.
This, along with her grabbing my ankles and pushing my
legs wide apart and back put my ass in the perfect
position. Without touching her cock, Michelle easily
zeroed in on my hole and was again buried to the hilt.
Once inside me, she pinned my knees back by my chest.
She was in complete control. I couldn't have moved
if I tried.
In and out - in and out - long thrusts, short hard
thrusts. Michelle was holding nothing back. In
this position I found I could easily stroke my own
cock while being fucked silly. All I could see in
the mirror now was Michelle - her blonde hair all
askew - and my knees and feet draped over her
shoulders. My sexy red toenails dangled in the air.
My tits now pulled to the outsides of my chest and
had flattened out a bit but none the less, they
continued to bounce with each thrust.
Michelle's thrusts became faster and shorter and I
knew she was about to blow her load deep in my bowels.
I couldn't wait! Suddenly Michelle's cock starting
throbbing inside me and I could feel jet after jet
of hot cum explode inside me. Michelle continued to
pound my ass. The cum only made me more slick and
lubricated. She was now completely withdrawing from
me and then driving her cock back in balls deep. I
felt light headed from all the sensations - then it
was over.
Michelle collapsed on the bed beside me. The last
thing I remember was the feeling of the cum oozing
from my ass and running down my leg. When I woke
up, it was 2:30 am. Michelle was lying in the
same position as when she collapsed. I had to
pee like a race horse and waddled into the bathroom.
Afterwards I found my nightgown and pulled it over my
head and boobs. With all that had happened in the
last 12 hours or so I needed sleep. I pulled a blanket
over Michelle and headed upstairs to my bed.
As I drifted off to sleep I could only think about
how completely satisfied I felt. That, and the
feeling of my newly acquired boobs pressing against
my chest as I laid on my stomach.
Part III - Coming Soon - Stay tuned for more fun and
excitement. We have several days of winter break to go!
Nadine
- 04.08.2022
- 17
- 0
