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30 Before 30 free porn video
30 Before 30
By RogerGirl
"Happy birthday, baby!" Chloe says to me as I wake up groggily in our
suite.
I roll out of bed and make my way into the bathroom. I stare into the
mirror and notice I look like a mess. My makeup is smeared; the veil
I'm wearing is torn and crumpled; and other than the veil and a garter,
I am completely naked. As I look at my reflection, I can't help but
think how much I've done in the past week. You see I'm not really a
woman and before this week I've never dressed as a woman before. I
suppose for you to understand how I got to this point; I will need to go
back to the beginning of the story.
My name is Cade Phillips and today is my thirtieth birthday. I have
always played things safe in life and have never taken many risks.
Growing up I never tried out for any sports teams, asked out the girls I
liked, went to any parties, or taken any advanced classes. I led a
relatively average existence that consisted of going to school,
graduating high school, getting into an average college, and getting an
average job. I never tried for any promotions at work and did my daily
duties without much recognition. Several years ago, something made me
change my ways. My best friend, Chad, was killed in a car accident and
like me had not accomplished much in his life. While at first I was
broken up over my friend's death, eventually it inspired me to make some
changes in mine. We had always discussed doing all kinds of crazy
things and at the time of his death we had accomplished none of them.
As I went online one day, I found these things called a '30 before 30'
list. People made lists of thirty things that they wanted to do before
they turned thirty.
Looking back on all of the stuff I had missed trying over the years, I
decided to make my own when I turned 26. The first several items were
pretty basic, but as the list went on I dug a little deeper. Here is
the final list of thirty that I came up with:
1. Try eating sushi.
2. Go to Vegas.
3. Ride a motorcycle.
4. Pull an all-nighter.
5. Go to a nightclub.
6. Learn how to play the guitar.
7. Ask out the woman at the Starbucks.
8. Dance in public.
9. Get a promotion.
10. Go to a concert or see my favorite DJs perform live.
11. Dress as a woman.
12. Have sex.
13. Get really drunk.
14. Sing karaoke in public.
15. Try out for a reality show.
16. Buy a car.
17. Tour Europe.
18. Go on a cruise.
19. Go bungee jumping or skydiving.
20. Ride a roller coaster.
21. Join a company sports team.
22. Get married.
23. Go on a road trip across the country.
24. Learn to surf.
25. Learn to snowboard.
26. Fly in a plane.
27. Go to a strip club.
28. Go to New York.
29. Go to Florida.
30. Visit the National Parks.
Over the next couple years, I began scratching off many of the items on
my list. Some of the stuff I found to be pretty enjoyable, while others
turned out to be things I'd never try again. I found that I enjoyed
playing the guitar, but riding a motorcycle wasn't really for me.
Having saved up quite a bit of money over the years and having
accumulated quite a bit of vacation time, I knocked out some of the
travel items over a couple summers. Several items I was able to combine
to save time, such as traveling to Europe and flying in a plane, and
volunteering for assignments at work that required me to travel helped
too. Soon I had completed half of my list, including getting a
promotion and buying a car, and decided it was time to ask out the woman
at the Starbucks. While I had been nervous about some of the other
items on the list, I was very reluctant to ask her out. I had developed
a sort of friendship with her over the past couple years and was afraid
of making things awkward between us by asking her out. I didn't even
know if she was single or not since I'd always been afraid to bring it
up.
"Hi Cade," she said as I walked in to order my morning latte.
"Morning Chloe," I responded.
We chatted about the usual topics as we waited in line for our drinks.
Chloe worked in an office across the street from the building I worked
in and we had been meeting almost every morning before work. When
Chloe's order was ready, I almost lost my nerve and let her leave
without asking her out. Instead, I decided to gather my courage and
make my move.
"Um, Chloe," I said as she headed toward the door.
"Yes?" she asked.
"Would you like to have lunch or dinner sometime?" I asked nervously.
"You mean like on a date?" she responded.
"Yeah, kind of like a date," I answered.
"Of course," she said smiling, "I was beginning to think you would never
ask me out."
That weekend we went out on our first date and Chloe told me that she'd
been hoping I'd ask her out for a while, but was starting to give up
hope. Soon after we went out on another date and not long after we
became a couple. I guess the saying that opposites attract is true
because Chloe and I couldn't be more different. While I was quiet and
reserved, Chloe was pretty adventurous and outgoing. After we started
dating, she encouraged me to complete some of the items on my list that
I had been more nervous to try. We went out to a bar one night and she
got me to sing karaoke on stage after a few drinks. It was pretty fun
and in the summer I auditioned for "American Idol," although I didn't
make it onto the show. On another weekend, we went skydiving and the
next weekend tried bungee jumping. Like riding a motorcycle, both of
them turned about to only be one time experiences.
After we had been dating a year and a half, I asked her to marry me and
she said yes. The wedding, however, would not be until after I had
turned thirty. There were only a few weeks until my birthday and there
were still eleven items left on my list. Since I was busy most of the
week at work, there wasn't much time to get everything done. That's
when Chloe came up with a plan.
"Listen, I was thinking about your list and I have an idea on how you
can finish the rest of our list in one night," she said.
"How is that?" I asked.
"Well, it's going to involve combining most of the items," she said,
"including dressing as a woman."
Many of you may wonder why that one is on my list. Shortly before Chad
was killed in the accident, we were invited to his cousin's gender
bender party. While we had both planned to go, I chickened out at the
last minute because I was afraid to dress up like a woman. I have
always been a small guy with soft features and didn't want people to
start making fun of me because I knew I would probably make a pretty
girl. Since I didn't go, Chad had to go to the party on his own and was
hit by a drunk driver on the way to the party. I always blamed myself
for the accident because if I had gone with him, Chad would have never
been driving in that part of town.
"So what is the plan?" I asked reluctantly knowing it might involve me
going out in public dressed as a woman.
"Leave that to me," she responded, "In the meantime you're going to need
to work on a few things."
Over the course of the next few weeks, Chloe had me prepare for the plan
whenever I had free time. I had my ears pierced and removed what little
body hair I had. With Chloe's help, I practiced walking in high heels,
putting on makeup, speaking in a female voice, and acting like a woman.
Meanwhile, Chloe was busy collecting items to transform me into a woman
for a night. Finally, the weekend of my thirtieth birthday arrived.
After we both got out of work on Friday we drove to Vegas. When we got
to the Aria, we went upstairs to the suite that Chloe had reserved and
were met by my sister, Chloe's sister, and a few of her closest friends.
"This is going to be so much fun," my sister Paige said as we walked in,
"I've always wanted a little sister."
Before I could figure out what was going on, we were all in a limo and
soon I found myself at a studio that does cross-dressing makeover
transformations. Chloe went to the counter and handed a woman several
bags of stuff she had bought and I was led to the back. The owner was
very friendly and we spoke as we went to the transformation area.
"So your girlfriend explained to me the situation," the owner said, "Is
this your first time?"
"Yes it is," I replied, "I'm a little nervous."
"Don't worry dear," she responded, "Just relax and enjoy being a woman
for a night. You might even like it. Is it OK if I call you Katie?"
"I suppose," I answered.
She explained the process and had me sit in the makeup chair. As she
began to apply my makeup, I tried to catch a glimpse of my reflection in
the mirror, but it had been covered. As she worked on my makeup,
another woman came by and began working on my finger and toenails.
After my makeup was finished and my nails were dry, she had me undress
and helped me attach a set of prosthetic breasts and a prosthetic
vagina. They were all very natural and realistic, and as I looked down
I saw the body of a sexy girl. Once everything was in place, she helped
me into a sexy bra and matching thong. Next, I put on a short white
dress that luckily didn't show off my new cleavage. It did, however,
show off my smooth sexy legs. After I was dressed, a blonde wig was
placed on my head and she did something to keep it in place. She
sprayed on some perfume, and helped me put on a bracelet, ring,
necklace, and a pair of earrings. Finally, she helped me step into a
pair of tan colored, open-toed high heels. The heels had a thick heel
and a strap that went around my ankle.
"Well are you ready to meet Katie?" she asked as I stood up and got used
to the heels.
"I think so," I replied nervously.
She led me over to a mirror and staring back at me was a gorgeous woman.
I smiled and noticed how sexy the woman's smile was. Maybe this won't
be too bad I thought to myself. The owner noticed my expression and
smiled.
"Now, have fun Katie," she said.
Before I left she handed me a white purse that Chloe had packed with a
few items I would need for the night. I stepped out to where the girls
were waiting and noticed Chloe wasn't with them. They all told me how
gorgeous I looked and that I would be seeing Chloe later. My sister
placed a sash on me and a veil on my head and smiled. I looked down and
the veil said 'bride to be.'
"What is this?" I asked confused.
"Tonight is your bachelorette party little sis," Paige replied.
They rushed me out to the limo and the six of us made our way out to
whatever Chloe had planned next. Thinking about the remaining nine
items on the list, I could only imagine where they were taking me. I
relaxed a little when our first stop was a sushi restaurant. The owners
congratulated me and sat us at a table that Chloe had reserved. The
sushi was pretty good and as the evening went on, I found myself feeling
like one of the girls. Everyone called me Katie and kept on mentioning
that Cole was a lucky guy for having found a bride as hot as I was. I
could only assume that Cole was Chloe. At least I hoped it was.
Surprisingly, we were also given drinks all night and I was never asked
for my ID. After dinner, we got back in the limo and made our way to a
new club where one of my favorite DJs was performing that night. We
were immediately let into the club and once again people congratulated
me. We posed for several pictures, including a couple with the DJ and I
had a good time letting loose and dancing with the rest of the girls.
At this point I was no longer feeling nervous about being out in public
dressed as a woman and had began thinking of myself as a woman out with
her bachelorettes for a fun night out.
By the time we left the club, there were only four items left on the
list. As I thought about the remaining items I suddenly realized what
we were going to do next and since I was a bachelorette for the night it
probably wouldn't be what I was hoping for when I wrote it. We made our
way into a strip club and the girls ordered me a lap dance. I sat very
still as a muscular cowboy began gyrating over me. I glanced at my
sister and she urged me to loosen up. I realized that I wouldn't have
to have any actual physical contact with the stripper, so I loosened up
a little and pretended to enjoy it. I slipped a few bills into his G-
string and eventually the lap dance was over. As we left, the girls
cheered me on for being a good sport and took me to a strip club with
women. They got me another lap dance, and this time I had to hold back
my enjoyment to avoid coming off as a lesbian.
Finally, we made our way back to the limo and soon we had arrived at a
chapel. We went inside and were led to a room where the girls and I
changed for the wedding. The people at the chapel knew of the situation
and told us it wasn't the first gender switch wedding they had
performed, but I was definitely one of the best looking gender-switched
brides that they had seen. I also got another shock when I saw my
parents and Chloe's parents waiting for me outside of the room where I
would be changing into a wedding gown. At first I was scared, but as I
looked at their faces they seemed happy. As my parents came over to me,
I found out that Chloe and Paige had explained everything to them. They
told me that they were proud of me for being willing to step so far out
of my comfort zone and try new things. They had both been pretty
cautious their entire lives, but seeing and hearing about what I had
done inspired them to create a list of their own and go out and
experience life. Since they were both retired and had money saved up,
they had a lot of free time on their hands to try some new things. They
both hugged me and my mom went with me and the other girls into the room
to help me into my gown.
Soon I was wearing a strapless wedding gown and it was time for my
wedding. I entered the chapel and as I walked down the aisle with my
father, I saw the girls standing on one side, their boyfriends,
husbands, and Chloe's brother on the other, and Chloe standing in the
middle. Except, the Chloe that was standing there was dressed like a
man. She had a shorthaired wig, a tuxedo, and fake facial hair. I
guess they were right about my marrying Cole. I reached the front of
the aisle and a short ceremony was performed. We placed the rings on
each other's fingers, mine being a woman's ring, and soon Cole lifted
the veil and kissed me as everyone cheered. After the ceremony, we made
our way down the aisle and posed for several pictures. Everyone
congratulated us and soon we were back in the limo and headed back to
our suite at the Aria.
When we got back to our suite, Cole was all over me. It turns out that
Chloe had made a list of her own and had been spending the night
scratching items off as well. The final item on her list was to see
what it was like to be with a girl. Even though she didn't consider
herself to be gay or even bisexual, she had for a long time been curious
to see what try sex with a girl. She was too nervous to try being with
a real woman, so she decided she would do it with me. Well, that night
I gave in and continued to play the girl and let her be the man. Soon I
was lying in bed wearing only my veil and garter and staring at me was
Cole's huge prosthetic penis. Like any woman on her wedding night, I
was ready and willing to please my new husband and gave him a night to
remember. Reluctantly I gave him a blow job and let him fuck me in both
the prosthetic vagina and in my ass. He was a strong, but gentle lover
and returned the affection by kissing his way down my entire body and
gently sucking on my nipples.
After several rounds as man and wife, Cole let me have a turn at my
fantasy. He went to the bathroom and when the door opened Chloe was
standing there wearing only a veil and a garter. She had removed the
penis, wig, fake chest, and facial hair, and her face was made up. She
got into bed with me and gave me a night of passionate lesbian sex.
Soon it was morning, and both of our lists were complete. We are both
exhausted and fall asleep in each other's embrace, which brings us to
where we came in.
I continue to stare at my reflection before rushing to the toilet to
pee. After all the drinks I had the night before, I have a lot to let
out. I wash my hands and brush my teeth, then put on a kimono and go
back to the room. Chloe helps me remove the breasts, wig, nail polish,
makeup, and vagina and I go back to the bathroom to take a shower. Even
though dressing like a woman wasn't as bad as I thought it would be, I
doubt it is something I will try again. Since we still have a day
before we have to go back to work, we decide to spend the rest of the
day in Vegas. This time of course it will be as Cade and Chloe. I get
dressed in some clothes that Chloe had packed for me and we switch
wedding rings. Even though we got married as Katie and Cole, we had
signed the marriage document with our real names and were legally
married.
Looking back at how much I have experienced since creating my list, I
feel like my life has only improved for the better. While I miss Chad,
I hope that in some way this list has honored him and that he is looking
down upon me with approval. Even though my '30 before 30' list is
complete, Chloe and I are planning a brand new list together as a
couple. Who knows, there may even be a spot for Katie and Cole on this
list.
Nova
- 25.05.2021
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