The Sitter
- 4 years ago
- 21
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House Sitter free porn video
One summer a friend of my mom's called and asked me if I wanted to watch
her house for a couple of week while she went on vacation. All I had to
do was bring in the mail everyday and water the plants. She offered to
pay me $200.00 while she was gone. The only bad thing about this gig was
that she lived 2 miles out of town in the country. That was OK though
cause I was driving now and it gave me an excuse to drive. She was even
nice enough to give me gas money. That was enough right there for me to
jump at this sweet deal.
The night before she left I went over so she could show me what needed
done. She showed me what plants to water and gave me her mail key and
where to put the mail. She also told me if I was bored I was more than
welcome to veg out and watch TV during the day if I wanted. She had a big
screen and a satellite dish so I knew I would take her up on that.
The first day after she left I went over and after finishing my chores
plopped myself down in front of the TV. I flipped through all the
channels, and after doing so decided on Dr. Phil. It was either that or
soap operas. That day on Dr. Phil he was interviewing men that like to
dress up like women. One of the men told his story about how he first
started dressing in his mother's and sister's clothes. He told Dr Phil
that every man has the desire to crossdress, and only a few men actually
dress. This sounded crazy to me. I had never thought about wearing
women's clothes, but the more he spoke the more I wanted to try it. I
guess maybe I wanted to prove the man on the show wrong.
I went into Kim's bedroom and I was a little surprised to see that she was
not a very neat person. That really blew my mind cause I thought all
women were neat freaks. At least my mom was. Well any way my plan was to
only put on a skirt to prove that I had no desire to dress like a woman.
After rummaging through a pile of clothes I found a skirt that I thought
would fit me. Kim is a very slim and beautiful woman. I knew she wasn't
much bigger than me so I was pretty sure her clothes would fit me. I
kicked off me shoes and took off my pants and put on her skirt. It was
hard to reach the zipper but I was finally able to zip the zipper up.
Then the weirdest thing happened to me. I never realized how soft and
silky a piece of clothing could feel. I decided that I liked the feel of
her skirt and stayed in the skirt for the rest of the day.
Over the next few days I started experimenting with more of her clothes.
I wore her panties and bras and her pantyhose. I was like a kid in a
candy store. The only thing that didn't fit me were her shoes. They were
about a size or two too small. That really bummed me out. I really
wanted to see what it was like to wear high heels.
That night I lay in bed wondering how I could get a pair of heels that fit
me. I thought about buying some but I knew I would never have enough
nerve to do that. Then I wondered if my mom would have a pair that would
fit. While she was watching TV downstairs I went into her room and
grabbed a pair. I took the shoes back to my room and locked my door. I
waited until my mom went to sleep before I put on her shoes. I was happy
to find that they fit like a glove. They were pretty black heels. They
were suede with a three inch spike heel. I was so happy that it was hard
for me to sleep that night. Tomorrow I was going to find out what it was
like to be completely dressed like a girl.
The next morning I told my mom I was spending the night with a friend so I
wouldn't be home till the next morning. I told her I was going over to
Kim's and then over to my friend for the night. I knew Kim would be home
tomorrow and this might be my last chance to dress in her clothes.
When I got to Kim's house that afternoon the first thing I did was take a
shower. It was hot outside and I was sweaty. While I was in the shower I
decided to shave off all the hair on my legs and underarms. I thought if
I was going to dress completely like a girl I wanted to make the most of
it. When I was done I walked into Kim's room to look for the perfect
dress I was going to wear . Until then I mainly wore her skirts and
dresses she would wear to work, nothing fancy. Well tucked back in the
far reaches of her closet was the dress. It was a black velvet dress.
Not too long and not too short. It had short sleeves and I could tell
this must have been a special dress cause it wasn't on the floor like her
other clothes. I knew this was the dress that wanted to wear for my final
day as Kim's house sitter. It was the most beautiful dress I had ever
seen.
I was now ready do get dressed. I found a pair of really sexy panties and
slid them up my legs. That felt so good. Next I found a black bra that
matched the panties and put that on next. I stuffed my bra with some
socks. I found a pair of black pantyhose and a gold ankle bracelet that
put on next. I had never worn pantyhose without any hair on my legs. It
was really an exciting experience in it's self. Next I found a sexy, lacy
black slip. That made me shiver all over when I slid it down my body. I
was really getting into this, I was having a good time. Before I put on
my dress I decided to put on some make-up. I didn't do too bad for my
first time. I even curled my hair. I had seen my mom curl hers a million
times so I knew how to curl mine. I was now ready to put on my dress. I
unzipped the dress and stepped into it. I had a hard time with the zipper
but used a piece of string to help guide the zipper up. Now for the first
time I was dressed from head to toe as a girl. I put on my mom's shoes
and wobbled over to a mirror to see how I looked. I was a little
disappointed cause I still looked like a guy in a dress, but I didn't
care. I just wanted to enjoy the moment.
When I finally got done dressing it was getting dark outside. I was
having a good time and I didn't want it to end. I got to thinking how
neat it would feel if I were to walk outside in the night air dressed the
way I was. I had never gone outside before. I knew nobody would be
around cause Kim lived outside of town. So I thought what the hell. I
looked around and found a purse that went with my dress and filled it with
my keys for my car and the keys to the house. I put my cell phone in my
purse and I was ready for my first time outside in a dress.
I was just about out the door when the phone rang. I almost wet myself.
I went over and answered the phone. It was just a stupid salesman trying
to sell me a windshield. After I got my bearings back I opened the back
door and stepped out into the night. I about fell over when I felt the
night air on my nylon clad legs. It was like a religious experience. It
felt so nice. I was till a little scared about being seen, but it wasn't
long before my fear left me and I was able to walk down to a stream. I
sat for a while and then decided to walk back to the house.
When I got back to the house it was already pretty late. When I got to
the back door the door was locked. Lucky I had my purse with my keys to
let me in. That's when I realized my purse wasn't on my shoulder. At
that time I didn't panic. I must have left my purse down at the stream.
I walked down to the stream but the purse wasn't there. It was then I
realized that I must have laid my purse down when the phone rang. When I
got back to the house I looked in the window and sure enough there was my
purse sitting right by the phone. The same purse that had my car keys and
my cell phone, and even worse the keys to the house. I was stuck outside
with no keys and no money. Worst of all I was wearing a dress and heels.
When I realized what had just happened to me I wanted to just die. I had
no idea what I was going to do. I guess I could have broken a window, but
I wouldn't have enough time to get it fixed before Kim got home. I knew I
had to get home before morning. I came to the very scary realization that
I had to walk home. It was a little more than two miles. Any normal day
I could make it home in about an hour. I knew it would take a long time
to get home wearing high heels and a dress. I knew it would take longer
cause I would have to take the back roads so I wouldn't have to be seen.
So I started to walk.
After the first mile my feet were killing me. I knew I wasn't going to
make it. I came upon a little store about a mile from my house. I saw
that it had a pay phone outside so I decided I would call someone to come
get me. I decided to call my good friend Julie. She was the only friend
that wouldn't laugh too hard or think I was some kind of freak. I called
Julie collect cause I didn't have any money on me, and I told her what I
had done and if she could come get me. I was wrong about how she would
react. She thought I was some type of pervert for dressing up in women's
clothes. She did say she would come get me though.
After what seemed like forever, Julie finally pulled up in her car. When
I got in the car the questions started. She asked me if I was gay? If I
wanted to be a girl? If I liked boys? I told her this was the last time
I would ever dress like this again. I told her I was being stupid and
never should have done this. Her mood and opinion changed after a while.
She said she was sorry for being nasty earlier. I told her all would be
forgiven if she would just get me home so I could get out of these
clothes.
When we finally got to my house it was pretty late. I got out the car and
walked up to the house and realized that I didn't have any keys to get in.
I knew I was going to wake up mom to let me in. I rang the door bell and
heard her making her way to the door. When she opened the door and saw me
dressed in a dress and her heels she wasn't very happy. In fact she was
pissed. I told her what had happen but the didn't make her any less
pissed. She told me I would have to stay dressed this way until tomorrow
when Kim gets home. I would have to explain why I was in her best dress
and in her underwear. I wanted to just die. I went to bed but I couldn't
sleep. When morning came my mom drove me over to Kim's. My mom had
called Kim before we drove over so Kim knew what I had done. She wasn't
very happy when we drove up to the house. The first thing Kim said was
that I just bought myself a dress and underwear. She told me how she had
trusted me and I let her down. I told her I was sorry , but that didn't
help. It was sad Cause I really liked Kim and I felt bad that she didn't
trust me anymore. The only good thing that happened was I finally got to
change back into my boy clothes.
After I changed my clothes I went with Kim to the mall. We went shopping
for a new dress for her to replace the one I had worn. After shopping for
a dress and a bra and panties it set me back about $150.00. I even took
Kim out to lunch. At lunch I told her how sorry I was and hoped we could
be friends again. I told her why I dressed in her clothes and how my
curiosity got the better of me. She finally warmed up to me and told me
she understood. She even told me I did a good job taking care of her
house. By the time we got home from shopping we were even laughing about
the whole thing. I was surprised when she said she would let me watch her
house again. She said that the next time I wore her clothes and decide to
go outside and get locked out, that I should just used the spare key she
keeps under the front mat. Oh well
Jayla
- 14.09.2022
- 22
- 0
