Housesitting
- 3 years ago
- 11
- 0
House Sitting free porn video
HOUSE SITTING
BY
DAWN MARIE
My name is Ron. I am seventeen going on eighteen but you wouldn't believe
it to look at me. I stand four feet and eleven and a half inches tall and
weigh in at one hundred pounds soaking wet with all my clothes on.
I live with my mother, like most families these days my father is absent
and has been for the last four years. I have a married sister, Sarah, and
a niece, (Her daughter), Carol, who is 12 years old and is my size; I
know this because a few months ago, Easter weekend, she left her Easter
dress here when they visited, and I tried it on one day when I was in a
cross dressing mood and it fit almost as if it was made for me.
As to the aforementioned "Cross dressing mood", I guess you can call me a
cross dresser because on occasion I like to get into my mothers clothes
and pretend I am a girl. The fact that I am so small and underdeveloped
for a guy my age I looked like a little girl playing grown up. I had been
doing this for at least five years and when Carol, my niece, left her
dress here I jumped at the chance to put it on.
I was both surprised and thrilled to see how cute I looked in clothes
that fit me, and with my long hair, how much I looked like a girl,
albeit, a little girl. I wore that dress almost every chance I got for
the next few weeks or so. I sometimes pretended I was Carol when in her
dress...I guess because I liked her so much, actually you might say I had
a crush on her but nothing could ever come of it because, one, she was my
niece, and two, she was about five years younger than me, or is it
younger than I?
In the middle of the summer Sarah and Carol wanted to go on an extended
vacation and asked me if I would house sit for them for about a month, it
would save the expense of putting the dog in a kennel and I could take
care of her plants and house.
I sort of jumped at the chance because I had nothing really to keep me
home, no friends or stuff like that...and I could indulge myself in
wearing girl's clothes that fit...Carols.
Mom dropped me off at Sarah's and took them to the airport after giving
me a list of stuff to do such as keep the house clean and water the
plants and dog stuff.
I gave them about an hour before running up to Carol's room and looking
through all her cloths to see what I was going to wear first. She had so
many nice things that I was difficult because she, Carol, is a clothes
horse. My plan was to wear a dress for an hour or two every day and then
maybe, after changing back, go to the mall and hang out for awhile.
ONE WEEK LATER.
I am standing in front of the full length mirror checking, for about the
tenth time, how I looked. I am wearing five pair of panties (Because they
give me the hips and an ass of a girl about twelve years old), a training
bra with about five or six cotton balls filling the small cups and a cute
cotton dress that comes to just below my knees. I am wearing just a
little pink lipstick and a touch of mascara; I want to look my best for
my first date with my twelve going on thirteen year old boyfriend. I
guess this deserves a bit of explanation.
The first dress I wore that day my mom drove my sister to the airport was
one of her party dresses. I wore it until bedtime and picked out what I
was going to wear the next day.
The plan was to take the dog for a walk, try on a dress or two, hit the
mall (Which was a twenty minute bus ride) for a few hours, come home and
just play things by ear until bedtime. Well, after taking the dog out I
started trying on dresses but I was so enwrapped in it that I lost all
track of time and it was supper time before I realized that I had tried
on almost every dress Carol had and I was hungry.
I took the dog out, watched TV and went to bed in my usual PJs, a tee
shirt and shorts.
Having worn almost all Carol's dresses I thought I might start on her
skirts and tops. The thrill was wearing off a little after three days and
I was no longer eager to change every hour or so. I was in a denim skirt,
which I liked wearing, and a tank top (I want to say here so that I don't
have to repeat every time that I wore the five pairs of briefs and the
padded training bra, OK)?
Every time I looked in the mirror I didn't see me, I saw a cute young
girl who I estimated to be about twelve, the same age as Carol. I
wondered how much fun it would be if I wore this outfit, the skirt and
top, when I took the dog out. I screwed up all my courage and did it, I
took him out for his walk in my skirt and top and no one ever gave me,
us, a second look.
The next day I did the craziest thing I had ever done, I steeled myself
and decided to go to the mall in a pair of carols shorts and a girl's tee
shirt with a teddy bear on the chest. I was scared all the way to the bus
stop on the corner, the bus ride to the mall and for about ten or so
minutes at the mall. Like with the dog walk, no one seemed to notice me;
this brought my courage and comfort factor way up, so far up that when I
was having a soda at the food court, which is in the game section, I say
a guy playing a video game which I am good at, and started giving him
some advice.
Actually what happened is that I was so comfortable with myself that I
forgot that I was dressed as a girl until I got up and stood next to him
that I saw my reflection in the shiny surface of the game. Oh well, once
done can't e undone.
I showed him how to do certain things to get extra points and we soon
became friends. We talked as we played and he seemed like a nice guy but
he was only twelve going on thirteen. I told him that my name was Dawn
Marie and I was... (I almost said seventeen)...twelve. His name
was...is...Benjamin.
I told him after a few hours that I had to catch the bus for home. He
walked me to the stop all the while holding my hand which I didn't notice
right away but when I did I did not let go. He asked if I would be back
the next day and I said I would, (I had no intention of doing so). I kept
giggling to myself all the way home and almost giggled like a girl a few
times.
I fell asleep thinking of how much I enjoyed my day, the first time in
maybe years that I could say I really enjoyed.
After taking the dog for his walk I talked myself into going back to the
mall sort of hoping that maybe Ben would be there and we could play some
more video games. (so much for no way I was ever going back). I stuffed a
bunch of quarters in my shoulder bag and headed out hoping that like
yesterday, I could present myself as a pre teen girl.
Immediately I entered the game room I saw Ben and waved to him. He waved
back and beckoned me to join him. He was sitting with a group of kids
seemingly our age, all pre teens, two girls and two guys. The girls
looked real cute and I kind of wished I met them in my real life; I would
have liked to be with them despite the five year age difference. I had a
soda, bought for me by Ben, and went to play some video games with Ben.
It was just like yesterday, we had so much fun time seemed to fly by and
this time I paid attention to his constantly touching me, which I think I
liked. He bought me another soda and walked me to the bus stop when I had
to go. We sat on the bench with him sitting as close as he could and me
liking it; I think I was so thrilled with having friends that I didn't
care that they were all pre teens and that one of them. Ben, had the
hot's for me. I got the feeling that when the bus came he wanted to kiss
me good-by, I don't know what I would have done had he tried but he
didn't so that was that.
That night I slept with one of Carol's big teddy bears in my arms and
dreamed that I was hugging Ben, which was scary...but good.
The next few days were pretty much the same, hanging at the mall with my
new friends. I really don't know how I got away with it, I guess I am a
convincing 12 year old girl, so much so that at times I almost had to
remind myself that I was in reality a seventeen year old boy.
Yesterday it happened, while waiting for my bus he asked me out to the
movies the next day, I accepted and then what I had been anticipating all
week happened, he kissed me goodbye. OMG that felt sooooo nice. It only
lasted a second or two at the most but to me it felt like hours. Is this
what I had been missing all my life?
On the ride home I was able to justify what I was doing. I had had no
childhood, no friends, either male or female, and now I did. It didn't
matter to me that they all thought I was a pretty pre teen like them, and
a girl. To me everything was cool and as long as I could get away with
it...I didn't care.
This brings me up to the beginning. Time seemed to stop for me and it
seemed that three o'clock would never come. I spent a lot of time in
front of the mirror checking and double checking to make sure I looked
terrific and I did. Last night I put nail polish on my finger and toe
nails and for the first time I used make up. I was getting nervous, half
of me wanted to back out and half of me wanted to get on with it, but the
foolish part won. It was time for me to catch the bus to meet Ben at the
mall where the theater was.
I met him as usual at the game room where he was talking to an older boy
of about sixteen. It turned out to be his brother. Ben had told me he had
a brother but that he was an ass hole.
When we were introduced he told Ben how lucky he was to get such a
hottie, I blushed at this. Rich, Ben's brother was cute and I liked him
from the first and he didn't strike me as and ass hole.
The movie was kind of fun, I didn't mind so much when Ben put his arm
around me, it was nothing new but when he kissed me again I thought to
pull away the first few times but soon got used to it and even enjoyed it
a little. Something in the back of my mind told me that this was not
right and I should be ashamed of myself but I was able to force the
thought out and went back to enjoying myself.
I didn't see much of the movie and was disappointed when it was time to
go. Sitting on the bus bench I kept hoping that it would never get here
but it soon did. Riding home I kept feeling his kisses and knew that I
had a boyfriend and how great it felt; too bad that I had to go back home
in three weeks and it would soon be over; I decided to take full
advantage of the situation as long as possible.
I spent more time each day with Ben, just the two of us, and sometimes we
would meet up with his brother, Rich. I liked meeting him because he
always told me how pretty I was and that if I was three years older he
would take me away from Ben, I sometimes thought that it might be nice to
have two guys fighting over me. Do all girls feel this way?
The night of my first date I moved into Carol's room, it was so feminine
and helped me feel more like a girl. I also started wearing my sister's
night gowns to bed because they were so sexy.
It was Ben's thirteenth birthday and a week before I was supposed to go
home. There was going to be a small party for him at his home. I had met
his parents a few times when Ben had me for supper and they seemed to
like me.
The girls all decided to wear party dresses for the party; this was cool
because it would give me a chance to wear one of carols fancy dresses out
of the house. I knew just the one I wanted to wear.
I had everything laid out the night before so that I wouldn't have to go
running around in the morning.
I could hardly wait until it was time for me to catch the bus to Ben's
house for his party. I bought him a game boy cartridge and when I gave it
to him I kissed him, I still found it just a little uncomfortable kissing
him, especially in front of everyone but I was getting used to it. Ben's
brother, Rich was there but on his way out. He again told me how pretty I
was and wanted me to go with him to watch a movie in his room. I was
tempted to do it, every time I saw Rich I liked him more and more and he
was starting to look cute to me. I wandered what it would be like to go
with a cute sixteen year old guy.
There were three other girls there and we had to admire each other's
dresses and tell each other how pretty they/we were. I had to admit that
Mary Anne Parker had the prettiest dress and I was a bit jealous of her
but what the hell...she was the prettiest girl there and I had a crush on
her. I wished I had know her before I decided to play at being a girl, I
may have put some moves on her even though she is five years younger than
I. could that have been any worse than what I am doing? A seventeen year
old guy playing at being a twelve year old girl and going with a thirteen
year old guy?
The party soon started and naturally the first game we played was that
old favorite, "Spin the bottle", but with a twist.
The twist was that no matter who the bottle pointed at, the person who
spun it had to kiss them; whether it be a boy or girl. I didn't quite
understand it until Ben spun it and it pointed to the guy next to me,
Ralph, and they kissed each other. It wasn't a real kiss, just lips
touching. Things were different when it was girl on girl though, they/we
kissed each for real, girls don't have that hang up, (Especially when one
of them is really a guy). I had more fun kissing the other girls,
especially when I had to kiss Mary Ann Parker.
We played for about an hour. The game broke up only after each person had
kissed the others at least once. I don't think the guys put everything
they had when kissing each other.
I had to take a piss real bad and hurried up stairs to the bathroom which
was between Ben and Ralph's room. Since I was wearing a dress that had
stiff netting to push the skirt I didn't wear but one pair of panties. I
let my guard down just once, I stood up to piss and as I finished I
turned to go and saw Ralph sitting on his bed watching me. I know he saw
everything because he was staring with open mouth. I knew I was dead
meat.
"Wow! My punk ass little brother has a "Chick with a dick" for a
girlfriend". He said. I was too shocked to say or do anything but stand
in front of him and stare.
Jeannie
- 18.06.2020
- 5
- 0
Houseboy for Hire
- 2 years ago
- 22
- 0
Treehouse Masters Teenage Love HutChapter 4
- 4 years ago
- 25
- 0
