Halloween Girl Chapter 1 Preperation
- 3 years ago
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Ashleys Halloween Prep free porn video
I was just hanging out at my friend Julies' house when out of the blue she
asked me what kind of plans I had for Halloween. I told her I didn't have
any plans, and then added why do you ask?
"Well" she said, "I was thinking we could enter that big Halloween costume
contest at the Clarion Hotel."
I said, "Hmm that sounds fun, what are you thinking about dressing up as?"
"Well," she said, "I was thinking we could go as hookers."
"Hookers, we?" I said. "What do you mean we?"
"It would be a great surprise, two sexy, attractive hookers and when we
get to the final we expose the fact that your guy! It would be a shoe-in
for a win!" she said.
"Well we have multiple problems here. First, I wouldn't make an attractive
woman. Second, I don't want to be a woman. And third, I don't know
anything about being a woman!"
"Come on Ashton, just do it for me!" she said.
"We wouldn't get past the first round with me dressed as a woman!"
"You would make a gorgeous woman, you have great bone structure, you have
good posture, and we're practically the same size as I am!" she said. "How
about if I can convince you would look great!"
I didn't say anything, but she just said, "come on!" And she took my hand
and led me to her bedroom. She told me to sit at the vanity and she
starting cleaning my face with a moistened facial pad. She pulled my hair
back and clipped it in place, she then starting rubbing foundation into my
skin. She then put on eyeliner, eye shadow, and mascara. She then outlined
my lips and filled them in with a very high gloss pink. She quickly
brushed some powder across my face. She then pulled my rather long hair
back and put it into some kind of bun on the back of my head. She left two
strands of hair dangling and grabbed the curling iron and added some curls
to the strands. Next she clipped on a beautiful set of dangling earrings.
She then turned me around and said, "What do you think?"
I was dumbfounded. As I looked in the mirror I could not believe that
beautiful girl was me. I was gorgeous!
This still doesn't mean that I would be a convincing woman. She said, "If
I can make you look like that in 25 minutes, what do you think I can with
5 weeks?"
"Okay, I'll do it! But no one can know about this?" I said.
"Great! We'll start right now!" she said.
"What, now? I can't start now."
"Why?" she asked. "What are you doing the rest of the day?"
"Well, I'm, err doing.....nothing," I said.
"Off to the bath then," and with that Julie starting running a warm bath
and she put in some wonderful smelling bath beads. I just stood there
waiting for her to leave, but she didn't. "What are you waiting for, get
undressed!"
"But you're in here, I can't get undressed in front of you."
"We're sisters now and girls get dressed and undressed in front of each
other all the time, so get busy," and with that I took off all of my
clothes and got into the tub. I was really enjoying the bath when Julie
came in and asked for one of my legs, she took the razor she was holding
and completely shaved the first leg, then the other."
"Now stand up," she said. As I stood up, Julie said, "Little excited are
we?" Julie then shaved what little hair I had on my chest, back, and butt.
She then took an electric clipper she grabed from the vanity and buzzed my
pubic hair and with the razor shaved it all off. I was completely shaved
from my neck down and it was very exciting. She looked at my dick and
said, "It's a good thing we're dressing you as a girl, because you don't
have much to work with as a guy!"
I blushed, but I knew she was right, I'm only about 3 inches long and not
very thick at all.
Julie then had me get out of the tub, she patted me dry and rubbed baby
oil into every part of my body. It was the most incredible feeling that I
have every experienced. I was totally turned on and any slight air
movement would make me feel a tingling sensations.
She then gave me the strangest bra I had ever seen. It had open cups and a
long torso portion with laces in the back. She had me slip my arms trough
the straps and she pulled the laces to tighten it. She then pulled all the
flesh on my chest where it hung over the opens cups. She then had me grab
the top of the door and she tightened the laces. Every time I exhaled she
tightened them again, after five iterations of this she tied off the
laces. She then gave me a pair of what she called thong control panties.
They looked like a stiff pair of thong panties, but when I put them on, it
separated and lifted my derriere and gave me a nice feminine form. She
gave me a silk blouse and a pair of Capri's and told me to put them on.
Next she gave me a pair of 4 inch wedge heels. She said, "I want you to
get used to having a feminine feeling to your body and you need some
practice walking in heels."
Julie said, "Let's go to the kitchen." We made a nice big pitcher of
margaritas and made our way out to the screened in porch where she pulled
out a joint. We poured ourselves a marg and she lit the doobie. As we
finished the joint, I realized how awesome the pot was, I was stoned and
feeling very horney. Every time I moved, the silk blouse would rub against
my nipples and send sexual shivers through my body. I was getting totally
turned on!
As Julie took a sip of her margarita, she said, "You look incredible -
you're very sexy and have a 100% natural look about you. Your tits are
amazing, you're at least a full B-cup and the way your nipples poke
through that blouse, it looks like you're totally turned on."
I had always been a little fleshy on my chest and Julie had always been a
little flat chested, so I guess to her it would look like I have nice
tits. She fired up another joint and I got really stoned. We made another
pitcher of margaritas and had just poured ourselves a fresh glass when the
doorbell rang.
I didn't think too much about it as Julie got up to answer the door, but
when she walked onto the screened-in porch with two guys, my stomach about
did a flip. She introduced the guys as Kevin and Mike, and she introduced
me as Ashley. As we poured them a marg, Kevin pulled out anther joint and
soon everyone was extremely stoned. It was getting a little breezy on the
porch, so Julie suggested we move inside to the family room. In the family
room there was a pit group and Kevin sat next to Julie, and Mike sat next
to me.
Julie turned on the tv and she played HBO's Real Sex from the dvr. A girl
was giving a guy a blowjob in the back of a taxi. Julie made the comment
that the guy had a nice cock. Kevin said it wasn't as nice as his. To
which Julie replied, "Let's see."
So Kevin pulled his cock out and it was bigger than the guys on TV, it
must have been 7 inches and it was extremely excited. Then Mike, who had
been getting closer and closer to me, leaned over and kissed me and for
some unknown reason I kissed him back. He then started playing with my
nipples, which totally turned me on and before I know what happened he had
my blouse open sucking on my tits. I look over and Julie is knelt between
Kevin's legs giving him a really intense blowjob. Mike takes my hand and
moves it to the bulge in his pants and I start rubbing him, he is
extremely hard and big. Next thing I know Mike undoes his pants and I
slide between his legs and start licking his cock. And before you know it
I'm giving him a really intensive blowjob as well. Mike yells I'm coming
and hot cum shoots into my mouth and starts running out my lips. I lick it
up with my tongue and just sit back and hold his cock in my mouth until it
gets soft. He pulls me up and hugs me and tells me how wonderful that was.
We all have another marg and talk about doing something later, but Julie
suggests that tomorrow would be better. They say okay they will call us
and leave. But not before Mike gives me a really wonderful kiss while
holding my ass tight. After the guys had left, Julie said we needed to
talk.
Julie asked, "What do you think about what happened?"
I told her, "I don't know why, but I feel very comfortable with everything
that went on."
I'm totally turned on by the way I look. I was totally turned on when Mike
was playing with my tits and sucking my nipples. I just loved giving him a
blowjob and tasting his cum in my mouth. Like I said, I don't know why I
feel this way, but I love the feeling and can't wait to experience more.
She said, that's great, I had a feeling you would react this way. Let's go
we have a few errands to run.
Julie pulls up to a hair and nail salon. She talks to the lady in charge
and she escorts me back to a chair. Before I know it, my hair is being
washed, cut, dyed, and curled. A nail tech is working attending to my
nails, where she is putting on a full set of acrylic nails and painting
them bright pink. Then the nail tech moves to my feet and starts giving me
a pedicure, finishing by painting them the same bright pink color. My hair
comes out of the dryer and is being styled by the stylist. Then finally a
different tech comes over and pierces my ears and installs beautiful
studs. Julie has been watching all of this and stands up and says
unbelievable!
The next stop is a shoe store called the "Wild Pair." The store
specializes in high heels. With the help of the shoe clerk, we determine
my size is a 9. Julie is directing most of the selection, and it appears
she believes I need shoes with a 5 inch heel. We leave with five pairs of
very sexy shoes in all types including wedge, sandals, mules, and pumps.
We also stop at Payless Shoes where we buy several pair of what Julie
calls casual heels (3 ? inches) plus a pair of pink and white tennis
shoes. Then we stop at Victoria's secret where we pick up several bras,
panties, camisoles, and pjs...then on to Plato's Closet for skirts, jeans,
shorts, and blouses. For make-up we went to Natural Women where I received
a color analysis, make-over, and complete kit of make-up. The last store
was an adult toy store. Julie selected three butt plugs in sizes small
medium, and large, and three realistic dildos in sizes small, medium, and
large. She also selected a set of Nipple suction bulbs with rings, three
adult dvds, and lots of lubricant.
"We're done shopping!" she said. "Let's get a drink."
When we finally get back to the house and Julie says its time for a few
lessons. She instructs me to remove my blouse and capris, and put on the
pair of sandals that strapped around the ankles and had 5 ? inch heels.
She then attached the suction bulbs to my nipples and turned it on. After
my nipples were sucked into the chamber she then slid the little rubber
ring down the chamber shaft and around the base of the nipple. When she
turned off the machine I was left with big nipples sensitive because the
rubber rings were around the base. She then started licking my nipples and
telling what beautiful tits I had. I was getting really turned on!
Julie told me to turn over on my belly. She pulled off my thong panty and
told me to pull up on my knees a little bit. She then started kissing my
ass cheeks and rubbing my hole with her finger. Al the while telling me
what a nice pussy I had. She then spread my cheeks and started tonguing my
hole, it was driving me crazy, I had never felt so excited in my life.
After about ten minutes I felt a cool lubricant and Julie's finger
entering me and it felt really good. After a few more minutes Julie told
me it was time for the small butt plug, she told me to push back when I
felt it on hole.
So I pushed back and it popped in and I gasped, it felt incredible. She
reached around and tweaked my nipples and kissed me on the neck. She asked
me how I liked the feeling and I said it was unbelievable and I was
totally turned on. She wrapped her hand around my cock and said, "My
aren't you hard."
She said okay enough of that and she pulled out the small one and pushed
the medium one into me. I thought I was going to explode, but she played
with my nipples and kissed my neck and told me how beautiful I was and I
got used to the feeling of the medium size plug. As I laid on the bed
enjoying the feeling of the butt plug, touching my nipples, thinking about
getting fucked by some stud, Julie left the room. When she returned she
was wearing a strap-on belt with one of the realistic dildos attached.
She told me it was time to learn to fuck like a woman. She removed the
butt plug from my ass and told me to get up on my knees a little more and
she moved in behind and started pushing the medium sized dildo, which was
about 7 inches in length, up against my hole. She said just take your time
and push back just like you did with the plug. So I did, but the dildo
wasn't tapered like the butt plug it was big all the way around. But she
kept on pushing and finally it entering me and I screaming like a little
girl! She kept on talking to me saying things like, "That's it baby you
know you want this cock, just keeping pushing back, you know you want this
cock in your pussy." After a few minutes she had the cock buried all the
way in me and she wasn't moving it, she was just letting me get used to
the fullness of it.
Then she grabbed a hold of my hips and started moving the cock in and out
of me. Easy at first then with a little more thrust and she reached around
and pulled on my nipples and I was totally into it! I had never felt so
excited ever! So then told me she wanted me to roll over on my back, so
without removing the dildo she flipped me over on my back and placed my
legs over her shoulders. She was then able to drive that fake cock deeper
into my pussy and she started banging harder and harder, pulling out
farther and farther, and driving deeper and deeper. I started breathing
really hard and she reached down and pulled on my nipples as she drove
that cock deep into my pussy and I screamed and started shooting cum all
over me! It hit my titties and even shot up on my face! She kept saying
does that feel good, you like being fucked like a woman don't you. And
with those final words she pulled out and I immediately felt like I was
empty and I was missing something. As I laid there trying to catch my
breath she said she was going to start me a bath and we had more to do
tonight.
After my bath Julie had me put on another open cup bra, a waist nipper
which she laced very tight, and a fresh pair of control thong panties. She
the handed me a silk baby doll nightie and told me to put on the 5 inch
mules we bought at the Wild Pair shoe store. She pulled my hair back into
a pony tail and told me to meet her in the living room. She started the
DVD player and the title that came on the screen was Blow-job Slut. It was
pretty blond woman giving a blowjob to a really handsome man. As the
actress was doing her thing Julie was commenting, "See how her hand
follows her lips up and down his cock," "See how she is swirling her
tongue on the underside of his cock," "See how she is gently squeezing his
balls," and on and on.
She was giving me a cock sucking class using this video. That video was
finally over and she put in the next dvd titled "She Likes it in Back"-
It was the same pretty blond woman from the first video, but this time it
was focused on her getting fucked in the ass. As the guy approached the
pretty blond, the pretty blond got on her hands and knees and spread her
ass cheeks. The guy starting licking her hole and the pretty blond cooed,
"Oh that feels so good!" The guy then lube her hole and started pressing
his cock into it and Julie started comment, "See how she pushes back,"
"See how the guy kind of picks her up and adjust her so he can get a good
deep fuck," "See how she matches his rhythm so she gets maximum
penetration," and Julie just continued to give me a thrust by thrust
commentary on the pretty blond woman getting fucked. I have to admit I was
thinking how I would incorporate some of the techniques into my next fuck
session. After the video was over Julie said time for bed and showed me
the way to the guest room. As I climbed into bed I was replaying the day
in my mind and just loving it. I quickly feel asleep and awoke to Julie
saying come on sleepy head its time to get up.
Julie helped me with my makeup and converted the bra I was wearing into a
halter style strap. She handed me a silk halter top and silk pair of
shorts both a bright tropical green print, then told me to slip on the
lime green wedge heels I bought at Payless and let's go. We went down to
the local Starbucks and ordered a couple of Lattes made with skimmed milk
and a lowfat blueberry muffin. She gave me a magazine to read and pulled
one out for herself. As we sat on the terrace reading Redbook and feeling
the cool breeze, I was really enjoying myself.
Then Julie announced it was time to go to the workout salon. We hopped
into her car and drove to a place called Curves. I went into the women's
locker room and Julie handed me a pair of tights and a leotard, and the
pink and white tennis shoes I bought the day before. She told me to change
in the stall, which I did. We did an hour of step aerobics that totally
kicked my butt, and then followed it up with floor exercises intended to
strengthen a girl where she needs it most, such as pelvic thrusts. Then we
came back to the locker room and she gave me a black bikini and a cover
up, she told me to go into the stall and change again, this time taking
off my bra, panties, waist nipper, and she helped me put my hair up and
slipped on a hair cover. I then followed her to spray on tanning booth. I
couldn't believe the tan lines I now had! It was very sexy! We then came
back to locker room and showered, each shower was a private stall, and
redressed in the silk halter and shorts. Julie helped me get my make-up
and hair back into suitable shape. Julie said let's get going we have to
get ready for our dates tonight.
As we drove Julie told me that Kevin had called that morning and they were
taking us to a really fancy wine-tasting dinner event. There would be a
seven course meal and each course would be served with a different wine,
so we need to have very pretty dresses for our dates. She pulled over to
this upscale dress shop and we went in. The saleslady asked what we wanted
and we explained we needed sexy little black cocktail dresses. She had me
stand on a little platform while she measured me and then produced three
very beautiful black dresses. I tried each one on and Julie said the
second dress would make Mike so hard he would be difficult for him to
stand up all evening. After I was done getting fitted for my dress, Julie
went through the same process, she also ended up with a gorgeous dress
that would make Kevin wanting the dinner to end so we could get back to
the house.
When we got home I started getting undressed and when I was down to my
panties and bra, Julie said I needed to come into the bathroom. Julie then
showed me how to douche. She mixed warm water with a liquid called
summer's eve and then she had me insert the end of the hose into my
bottom. She told me that it would clean me out and get me ready for sex. I
then watched as she did the same thing for both her pussy and bottom. And
I thought to myself how lucky she is to have two ways to satisfy Kevin.
Julie handed me a black corset with open cups and I slipped it on. She
then had me turn around and she laced it up. She had me grab the top of
the door and every time I exhaled she pulled the laces tighter until
finally she said that was good enough. She then had me lace her into her
own corset and we went through the same exercise with her. Dangling from
the bottom of our corsets where garters, so we pulled thigh-hi hose up our
legs and attached the tops to the garters. I then pulled on a matching
black thong panty. I then slid my sexy little black dress over my head and
settled it in place. I selected my sexist pair of black sandals with thin
straps and a five inch heels and fastened them to my feet. As I looked
over I could see that Julie was done getting dressed as well. She handed
me a little clutch purse and told me it was time to go to the salon for
our makeup and hair.
As we walked into the salon the lady working the desk said, "Well aren't
you two looking fine tonight?" She then took us each back to a chair and
two different girls started on us. They did a wonderful job giving us very
dramatic looks and very elegant hairstyles. We were ready for a night on
the town and not too soon as Kevin and Mike pulled up to pick us up.
Mike walked up to me and gave me a big hug and kiss and said you look
incredible. You are extremely sexy and beautiful. That dress accentuates
your every curve and he leaned over again and I could feel his hard cock
pressing against my leg. Kevin had similar compliments for Julie. And off
we went to the restaurant for dinner.
Dinner was fabulous! It started with a very beautiful white wine while
waiting for our table. Then a different wine came with the appetizer and
so on. The main course was chateaubriand which was perfectly prepared. In
all we had about 7 glasses of wine and a beautiful time. We were talking
and laughing, and I felt very comfortable and safe with Mike. So when the
dinner extravaganza was over Julie and I suggested we go back to the
house.
On the ride to the house I snuggled up to Mike and he put his arm around
me and nibbled on my ear. As soon as we walked into the house he turned me
around and kissed me very deeply and I kissed him back. Julie and Kevin
were already in her room and I suggested Mike and I do the same.
As we stepped inside my room Mike came up behind and placed his arms
around my waist and slowly moved up body until he cupped my breasts, all
the while kissing my neck. I turned around and kissed him deeply and then
rubbed his cock through his pants. I slipped his jacket off and unbuttoned
his shirt, then pulled his shirt tail out. I turned around and lifted up
my hair and asked him to unzip my dress, which he did. I slowly slipped
out of my dress and stood there in the open cup black corset, with
stockings connected to the garters, and 5 inch high heels. He said I was
incredibly sexy and came towards me and I undid his belt and started to
slip his pants down, which he quickly finished and then pulled his boxers
down and he took them off. I grabbed a hold of his cock and started to rub
it with my hand and then I licked the head tasting some pre-cum. I then
leaned up and kissed him on the lips and told him I wanted him to make
love to me. He said he would love that very much.
I moved on to my hands and knees, and he pulled down my thong panty. And
he started kissing my ass cheeks and spread the cheeks and starting
licking my rosebud. He was telling what a beautiful ass I had and how he
found it so sexy. He then asked if I had any lube and I reached in the
night stand and found a bottle, Julie must have placed it there for us. He
then inserted a lubed finger into my hole and said oh yes very nice and
tight. A little more of that and he was ready. He placed his big cock head
on my hole and pushed and I pushed back just like Julie taught me and his
cock popped in and I gasped out loud. He waited for a few minutes and
started stroking his massive cock into my sweet tight hole. He reached
around and pulled on my titties and told me how good it felt, and I
noticed he started stroking faster and pulling me closer to him and
thrusting harder and harder, and then he grunted and I felt hot cum being
pumped in to my hole. It was so exciting my cock shot a load of cum into
my thong panties. And we both kind of collapsed into each other.
He soon was asleep and I got up to clean myself up a little. Julie must've
heard me, because se came into the bathroom and wanted to know how it
went. I told her it was the best sex I ever had, and hugged her and
thanked her for helping me so much. She said we were sisters and that's
what sisters do. She told me to put a tampon in to soak up the cum so it
wouldn't run down my leg. She helped me out of the corset and I put on the
bra, waist nipper, and panties I was wearing earlier and slipped on a
fresh baby doll and went back to bed with my man. Mike woke up early with
a hard on, so I gave him a blowjob and he went back to sleep.
Around 10 am both Julie and I got up and starting making breakfast. I'm
sure it was a sexy sight, two beautiful girls in sexy baby dolls making
eggs and bacon. Soon the guys were up and we fed them and sent them on
their way, but not before making plans for later that night.
After the boys left Julie and I were sitting on the screened in porch
finishing our coffees, Julie asked me, "So do you think you could pull off
being a woman for the Halloween party?"
I just had to laugh and said, "Yes I think I can!"
Then Julie turned serious and said, "Where do you see this going?"
And I told her I had thought about that and I couldn't see myself in my
old role again, but wasn't sure how I was going to proceed.
She said, "You know since we both have the summer off, why don't you move
in as my room mate and I can help you work through this?"
I said, "That sounds like an excellent first step. I know I want to live
full-time as a girl, I'm even thinking about picking up a waitress job or
something to really experience being a woman."
She told me that a local bar and grill was hiring bartenders and that I
should apply.
Julie then asked me what I liked the most about being a woman, and I told
her that I loved the attention, I loved looking sexy, I loved having my
nipples sucked, I loved getting fucked, but most of all I love sucking
cocks. She couldn't have agreed with me more, and she said, "You know that
makes us a couple of sluts, very beautiful and sexy sluts mind you, but
sluts just the same."
I said, "I know and I love it!!"
If you liked this story, please email at [email protected] and let me know
your thoughts. It means a lot to me when others tell me what they think of
my stories. Love Ashley
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