Blind Date with a Mistress
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I Am My Brothers Mistress free porn video
I AM MY BROTHER'S MISTRESS.
BY
JANICE
My name is Gerald, I am fifteen. I have a twenty year old brother Fred,*
who lives on his own, my parents work and I spend a lot of time home
alone.
*Fred is not my real brother, when our parents married they were told
that they could not have any children so they adopted and thanks to
modern medicine, five years later, along came Gerald.
For the past two years, since my brother, Fred, left home, I have been,
occasionally, wearing my mother's clothes. I know I looked like a little
girl wearing her mothers clothes because she is bigger than I. I did
have a few skirts and a dress of my own that I bought with my allowance
and keep hidden in the crawl space to the attic above my room.
It was the second week of summer. I would spend several hours in my girl
things because I had all day to do it. This particular day I was wearing
my own denim skirt and a tank top. I had one of my mothers bras stuffed
with socks on; I could never bring myself to buy my own girl's under
things so I wore hers even though they were large.
In my eyes I was a pretty good looking girl with the skirt and top and
wig which I had bought at a garage sale last Halloween. The only make up
I ever wore was some lipstick.
I was sitting on the couch watching TV and must have dozed off because
the next thing I knew the door opened and my brother walked in.
He looked at me for a second, "I have to use the bathroom," he said and
ran to the bathroom. I knew he had seen me so I just stood there in the
living room trying to think of a logical reason why I was dressed as a
girl. None came.
I was still standing there when he finished. He looked me over, "Not
bad," he said. "A little work and you could be pretty. Care to tell me
why you are in that outfit?"
I was soooo busted. I could do nothing but tell the truth. I told him
how I liked wearing girl's clothes and a long story but I will leave
that, it is of no import to this story.
I was relieved when he said, "Cool." That is all, "Cool." I asked if I
should change. He said he didn't care but he liked seeing me as his
sister. He was a computer repair man and had a call in the neighborhood
when he had to go to the bathroom.
He spent a little over an hour with me. He kept telling me how pretty I
was as a girl and I felt soooo good when he did.
When he was ready to leave I walked him to the door. "I hope to be
seeing more of .....? Do you have a girl name?" he asked. I told him I
didn't.
"You do now, it's Grace," he said. At the door he took me in his arms
and kissed me full on my lips. "I hope I can see you again in two
days...Grace," he said as he stepped back and went out.
I was at a loss for words. My brother and I had always been close but
this was different. And I liked it. I felt his kiss the rest of the day.
The following night Fred called and told me he would be at my house at
ten in the morning and he wanted to see Grace. I was so glad that he did
not hate me for being weird.
By the time he arrived I was in my best, and only, dress. It was a black
sleeveless dress with a high neck and a skirt that came to just below my
knees. I thought I looked good in it and so did Fred when he saw me.
He kissed me at the door. I was nervous. I really did not know what he
wanted. He told me that when he first saw me in that skirt and top the
other day, he thought I was beautiful and he knew that I was the girl
for him. I was red with embarrassment. I never looked at myself as a
girl; I was simply a boy who liked dressing as a girl.
We spent the rest of the day just talking, sort of feeling each other
out you might say. When he left that day he did not kiss me, we kissed
each other.
For the next month we saw each other about two or three times a week. He
almost always brought me something feminine. He even brought me several
bras my size, oh! How different it felt wearing a bra that fit right. We
became what I liked to call, "House bound lovers." We never went out of
the house but we did become as intimate as two can be without having
sex.
During that month I practiced using make up and made some hip padding to
make me look shapelier.
One day he stayed for supper. I had to change back to regular li'l old
me before my parents came home.
During supper he asked mom and dad if I could spend the weekend with
him, on a fishing trip. Now I didn't like fishing that much but I had
done some with my dad and Fred when I was younger so I said I would like
to go if it was alright with them. He asked me to walk him to the car
when he left. He told me that there was no "fishing trip." He wanted me
to spend the weekend as Grace. We had been talking about me spending
more than a few hours as grace, and maybe going outside the house. I was
more than willing, I almost kissed him but knew that would be a no-no;
we tried to keep our lives separate.
I was ready and packed when Fred picked me up at 4pm that Friday. I had
packed my one and only black dress and the few skirts I owned, plus the
bras and panties I had the ones that Fred had bought me. I also packed a
lot of my regular things so mom would see that there was some stuff
missing.
A little information is needed here. Fred had, for the past six months,
a female room mate. She had just moved out and left a few of her things
that Fred assumed would fit me. He said that there were enough for me to
wear for several days; we would be back from our "Fishing trip" Sunday
night. This would give me one full day, Saturday, and part of today and
Sunday. Need I say that I was looking forward to it?
Fred lived on the second floor of a five story building. We arrived and
got everything to his apartment. He showed me my room, his ex-room
mates, and told me to change and I could look for something of Vera's
that may fit me. I looked through her stuff and saw quite a few things I
would like to try on, but maybe later.
I put my things away, my girl things in the proper places and my guy
things in my backpack under my bed. I took a shower and sorted out what
I wanted to wear. I settled on a white tee shirt and a short, black,
wrap around skirt that was Vera's.
For the first time in my life I was a girl from the skin out. The skirt
fit me right so I assumed that all her things would fit. I brushed my
long hair, put on a bit of lipstick and went to the living room to join
Fred.
He looked at me and said I looked great.
I stepped into his arms and we finally kissed. I thought I felt
something hard between us as he crushed me to him, I realized I had a
hard on, must do something about that.
"I'm going to take a shower. I ordered pizza. Pay the guy when he comes.
The money is on the table."
"I can't answer the door dressed like this, what will he think?"
"He'll think a girl is paying him. What else would he think?"
"But I'm wearing girl's clothes. He will think I'm weird," I said. I
never thought that other people would see me in girls' clothes.
"Just pay him." Was all Fred said. He went to the bathroom and I sat
nervously waiting for the pizza. When it did come I was almost too
petrified to move but I managed to open the door. The guy never gave me
a second glance as he handed me the pizza and I handed him the money. He
gave me a nice smile and called me Ma'am.
"See. There is nothing to worry about. He never would think that you are
not what you look like, a pretty girl. Now, let's see what we can do to
that Pizza."
We did a job on that pizza and soda. We pigged out. I cleaned off the
table and we went to the living room to watch some TV before bed.
Bed, what were the arrangements? I had never spent the night here, was I
going to sleep with Fred? Or was I going to sleep in the spare room? I
don't think I was ready to sleep with Fred because I was not sure
exactly what this new relationship was.
He was sitting on the couch when I finished straightening up the
kitchen. He patted the seat next to him. I went over and sat. He put his
arm around me and for the next few hours we watched TV, cuddled and did
some light petting.
About nine thirty I went to the spare room to change for bed. I had been
grace now for about six hours; more than ever before and I had another
two days. I was thrilled.
I then realized that, typical for a guy, I neglected to pack something
to sleep in. At home I always slept in my underwear. I guessed I could
do that there but who's underwear? My, Gerald, tee shirt and boxers
(which I was not wearing at that time) or grace's bra and panties, which
I was?
I looked through the drawers to see if his ex-room mate, Vera, had left
anything I could use; I was in luck. I found a drawer almost full of
assorted sleep wear. I picked out a top and pajama pants but no robe, I
did find a couple pair of fuzzy slippers.
I took off my skirt and top and put on the white tank top and blue
pajama pants. I did leave my bra on because without it, I would have no
boobs.
I found some curlers and rolled them up in my hair. Now I had no idea
what I was doing but wanted to see how it felt. I had seen my mother
wearing them to bed a lot and this weekend I was a girl and I wanted to
experience being one in as many ways as I could.
In the bathroom I saw one of Fred's shirts and thought I would wear it
as a robe. Did I tell you how big Fred is? He is huge and his shirt fit
me like a dress; the tail was so long it came to below my knees and the
sleeves covered my hands and then some.
I went back to the living room, "Hope you don't mind, I forgot to pack a
robe," I said indicating the shirt.
"Not at all," he said, "Vera used to do it all the time. You look sexy
in it." We watched TV for a while then decided to go to bed. Hand in
hand we walked down the hall to our bed rooms which were across the hall
from each other.
"Good night love," he said, kissed me and went to his room. I went to
mine and crawled into bed but first I grabbed one of the many teddy
bears that Vera had left behind. For the first time since I was three,
I slept cuddling a Teddy Bear. It was a bit different sleeping with a
head full of curlers and sometime during the night I removed them.
I awoke to the smell of coffee. I crawled out of bed, put on my "robe"
and went to the kitchen. Fred was sitting at the table with a cup of
coffee in front of him. I bent down and kissed him good morning.
"I have a few calls to make and should be back by noon. Make yourself
comfortable and look around. When I am back we will go for lunch and do
some shopping for some more clothes for you, OK?" he said as I poured
myself a cup of coffee.
"Works for me," I said. He finished breakfast and left.
Vera did not leave a lot of things but I did find something in the
closet that I simply loved and wished there was a reason to wear. It was
a beautiful evening gown. I held it against me, as I had seen girls do.
I knew I had to try it on, and I did.
It was so beautiful and felt so good on me. There is a difference
between putting something on and wearing something. If the gown looked,
and felt, so good just trying it on; how great will it be wearing it?
I kept it on for about twenty minutes before changing into regular
(girl's) clothes.
I found a long peasant skirt and a top. My eyes kept going back to the
gown so I put it back in the closet, way in the back so I couldn't see
it. I cleaned the apartment, which wasn't hard because Fred is neat and
clean. I did one thing I always wanted to do when in drag, I put nail
polish on, and a spritz of perfume, both things Vera had left.
I had a bag of trash and had to take it out to the garbage chute.
Since I started dressing a few years ago I had read a lot of stories
about cross-dressing on line. In most of them the guy gets all paranoid
when he has to go out the first time, I was not nervous when I took the
garbage out, although all I had to go was down the hall. I just put it
in the chute and started back when a girl came out of the door next to
mine. I held the chute door open for her.
She smiled at me, thanked me and stood there as if she wanted to talk.
"I'm Marcia. I have never seen you before?" It was more of a question
that a statement.
"I'm Grace. I'm staying with my...brother. Fred, for the weekend." I
didn't know if Fred was my brother or lover, I settled on brother to
avoid any complications; after all, there is a five year difference in
our ages. How would it look for a fifteen year old girl to be staying
with a twenty year old "lover"?
We talked for a few minutes and went to our own apartments.
About an hour later the door bell rang. It was Marcia. She said she
wanted to get acquainted.
I guess I should have been nervous, (according to the stories) but I
wasn't. I liked Marcia and we became friend in that short time.
I told her that as far as I knew I was only staying here for this
weekend and did not know if I would ever be back. I hoped I would. It
was about eleven am and I had been grace since about five last night and
still had over twenty four hours before becoming Gerald again, and...I
was having the time of my life; even if all I was doing was talking to a
girl while dressed in a peasant skirt and top. She left and I watched TV
till Fred came home.
Like a dutiful wife or girlfriend, I met him at the door with a hug and
kiss. He handed me a small box, a little smaller than a shoe box.
"I thought you might like these," he said.
I opened the box and found a realistic pair of breasts. I had seen them
on the internet and knew what they were. There was also a bottle of
spirit gum to hold them in place. I took off my top and bra, applied the
glue and placed them on my chest when the stuff got tacky. I knew the
glue was not the semi-permanent kind that works for months, and I could
simply peel these off when I wanted to.
They made quite a difference in my bust measurements and I did like the
extra weight they afforded when I put my bra and top back on.
I told him that I met Marcia, from next door. He said that was good
because it was nice for me for the next time I came; I could have
someone to be with other than him. I made it a point to tell him that I
told her I was his sister, not his lover and especially not his brother.
He changed clothes and told me that we were going shopping for some
clothes more suited for a fifteen year old girl. He said that I could
not keep wearing Vera's things. By this I assumed (correctly) that there
would be more weekends like this.
We first went to a burger place for lunch, and then we went shopping.
He determined that no girl has all new things so he took me to a thrift
shop and bought a lot of used dresses, skirts and other cool stuff so
that I did not have to wear dresses and skirts all the time; not that I
would mind.
Back home I put my stuff away in dressers and the closet. I again saw
that beautiful gown and just caressed it. I wished there was a way I
could actually wear it, but where would that be? And when?
He told me to find something fancy to wear because we were going out for
dinner. I knew it wouldn't be fancy enough for that gown so I picked out
one of my new dresses. This one was basic black and I liked it from the
minute I tried it on at the shop.
I was standing in front of the mirror in just my panties and bra putting
on my make up when Fred came out of the shower and stood behind me. He
kissed the back of my neck. I turned and saw that he was naked. I looked
down and saw that his cock was huge, one of the hugest I had ever seen;
not that I see that many cocks. I thought to myself that a cock that big
must almost split a woman in half. He asked me if I wanted to touch it.
I refused.
He got dressed while I finished my make up and put on my dress. It took
me awhile to get my hair just right because I had very little experience
doing it. I usually just wore it in a ponytail. I kept thinking about
the size of his cock and how lucky I was that I was not a girl and might
be getting that stuck in me after this "date" tonight. I was thinking
just like a girl.
Fred told me that I had never looked prettier; I thought he was right.
From his conversation this afternoon I knew there would be more weekends
like this so I decided to see if I could get a book of hairdos and
practice on myself at home.
He put his arm around my waist as we walked to the car. We did meet
Marcia in the hall. She told me how pretty I was. She did give us a
funny look when she saw how close we held each other.
He drove to a high class Italian restaurant, not so high class as that
the women wore gowns but did wear fancy dresses. I felt right in place.
We did need reservations, which Fred had made earlier.
We were seated by a host who met us at the door.
I knew I looked much older that my fifteen years because the Matre de
asked if I, we, would like a drink before ordering. I have never had
alcohol but this night was so special that I asked Fred to order one for
me. He ordered something called a "Shirley Temple." I don't know what
was in it but it was good, I had a total of three that night and can
proudly say that they didn't affect me in the least.
Fred treated me just like a real, grown up, woman. We even danced a few
times.
The food was delicious and the dancing fun. During some of the dancing
we were so close that I felt I had a hard on; fortunately, I always wore
a panty girdle when dressed like Grace, always; because when her, I
almost always got a hard on from time to time.
All too soon, we had to go home. I was almost shocked to see that it was
a little after midnight already. I thought it was no later than nine or
nine thirty; I wonder if it was the: "Shirley Temples"
Fred drove home with one hand on the wheel and the other arm around my
shoulder holding me tight. I enjoyed being cuddled that way.
I was very tired but did not want the night to end so I stayed in my
dress as long as I could. Fred said he was going to get ready for bed
and went to his room to change, I followed him.
He got naked in front of me. I wondered how he saw me there, did he see
his brother, or did he see a beautiful girl whose pants he had no chance
of getting into for reasons that were obvious.
I again looked at his huge cock and was again glad I was not a girl who
may be getting that monstrosity stuck up her pussy after a night on the
town. He saw me looking at it.
"Did you ever see one this big before little brother?" I guess that
answered my question. I felt bad a little; I wanted to be seen as the
girl I felt like. He must have seen a look on my face because he took me
in his arms and kissed me.
"I'm sorry sweetheart. I'll never make that mistake again." He kissed me
again and this time I knew he did not see his "little brother." I felt
his tongue enter my mouth. Never having been kissed like this I did not
know what to do, I just let him do what he wanted; I accepted him.
I soon felt that my cock was getting so hard that it might burst the
girdle I was wearing. He was kissing me and dry humping me at the same
time. If this is what ecstasy is, I'm all for it. I felt a warm
stickiness in my panties and knew that I had cum in them. I still did
not pull away from him for awhile. Finally I lost all my strength and
sort of lost my knees.
He held me up until I was able to gain my composure. "Wow!" I moaned,
"That was the greatest thing I ever felt." I was still a bit short of
breath.
He was still holding me in his arms. I felt him unzip the back of my
dress. We parted just enough for him to pull my dress off and let it
fall to the floor.
A few more kisses as he squeezed my panty hose clad ass.
He was completely naked and I was in my bra, pantyhose, panties and
girdle. He pulled my pantyhose dawn a bit.
"I'll take it from here," I said. I picked up my dress from the floor
and went to my room. I removed my pantyhose, panties and girdle. Sure
enough it was all wet and sticky. I cleaned myself off in the bathroom
and went back to my room where I looked for something to put on for bed.
I found a short, sexy, baby doll nighty. I changed my bra for a sleep
bra. And put on the nighty. It was really short, to just below my
crotch, barely.
I was looking at myself in the mirror when Fred came in my room.
"Just want to say goodnight," he said. He was wearing a pair of pajama
pants.
I turned and he kissed me goodnight. I will never know why but I reached
between us and grabbed his cock, I felt it get hard as I held it. It was
a handful.
"You look beautiful in that. It is, was, one of Vera's favorites. She
wore it a lot."
I let go of his cock to put my arms around his neck. He grabbed my waste
and lifted me up and sat me on my dresser.
My cock was as hard as his, but nowhere as big. He saw it pushing
against my gown. He pulled it out of the waist of my panties, looked at
it and got to his knees.
His head was even with the top of the dresser.
He pushed my knees apart, put his lips around my penis and gave me the
first blow job I ever had. He soon had the whole thing in his mouth and
was thrusting his head up and down. I matched his rhythm as I held his
head in my hands until, with a burst, I came in his mouth. I felt his
tongue licking all the cum from my now softening penis. I felt drained
as he stood back up licking what was left off his lips.
I stuffed my now soft prick back in my panties as I got off the dresser
top and stood on the floor.
"That was great," he said to me. "Now I think we better get some sleep.
I'm beat."
"Me too," I said. "Let's get to bed."
I reached into his pajama pants through the fly and grabbed his cock. I
led him through my room across the hall to his room and held it while we
both got into his bed. Need I say that it was a lot bigger by the time
we got to his room than it was when I first grabbed it?
I woke up the next morning in his arms in what I later found out to be
the "Spoon" position. I glanced at the clock and saw that it was just
before ten AM. I quickly woke Fred.
I had never slept this late and thought maybe it was the Shirley Temples
that did it. It would be many weeks before I found out that a Shirley
Temple had no alcohol whatever.
We put our robes on, my gown came with a sheer robe that was no longer
than my gown and hid nothing. We had a cup of coffee.
"Should I make some eggs?" I asked Fred.
"No girlfriend of mine is going to cook on a weekend. Why don't you put
on one of your new dresses and we can go for brunch?"
This sounded good to me so we thought we should shower, together.
We showered together washing each other from head to toe. I took a long
time washing his penis because of how big it was and because I loved the
way it throbbed every time I touched it.
The worst, or was it the best, thing he did to me was to stick his soapy
fingers up my ass. It felt so dammed good and when he did, I got a hard
on. His fingers were tight at first but I soon got used to it, I was if
fact glad that it was his fingers, sometimes he used two, instead of
that huge, humongous Wang he had between his legs.
It was not only the longest, but the most enjoyable shower I ever had.
We dried each other off and went to our respective rooms to get dressed.
Knowing that this may be my last time dressing as thorough as I was, I
took a long time doing it right. I wore the finest pair of panties and
bra I had. I was especially careful of my padding and pantyhose. I knew
just which dress I was going to wear, I bought it yesterday just for
today. I did what I could with my hair; all I had to work with was
hairspray because in a few hours I had to put it back the way Gerald
wore his. (Did you see what I just did? I just referred to myself as
another person.)
My dress was hanging on a hanger on the closet door. Like a schoolgirl I
took it down and held it against myself.
I pulled it over my head and smoothed it over my body so that each and
every curve was accented. I don't think I ever looked so beautiful. I
stepped into my black 2 inch high heel shoes, the only pair I owned, I
bought them yesterday. Must get me a few more pairs, that is if this is
not the only weekend as Grace; and from the way Fred was talking, it is
the first of many. Satisfied that I was a beautiful as I will ever be, I
walked out to the living room and presented myself to my lover, Fred.
"My God, you are beautiful," he said as he took me in his arms and
kissed me.
We drove to a diner and had a wonderful brunch and then took a long walk
in a beautiful park full of lovers, like us. After a few hours it was
time.
He drove us home so I could change and return to Gerald. We took the
elevator to our floor and held a kiss the entire time. As the door
opened Marcia was there waiting, I presume, for the elevator. She got a
real good look at us kissing; not as brother and sister, but as lovers.
It is a good thing she was in a hurry or she might want to talk to me. I
could see many questions in her eyes that I did not, could not, answer.
A long hot shower later and my hair was all loose as Gerald wore it,
then another hour getting my nail polish off, and grace was gone.
Of all the clothes we bought, all I took with me was two denim skirts
and a few tops which I knew I could hide. There was an entrance to the
attic in a closet in my bedroom, which is where I kept my girls things.
On the long drive home I sat cuddled in Fred's arm cuddling next to him.
He was wearing loose shorts, as was I, and my hand was rubbing his inner
thigh. I reached in his fly and withdrew his prick and played with it
awhile. It gets so hard so easily. I was playing with it as if it was a
joystick. Moving it right or left to make turns and forward for more
speed, I don't know how he kept the road. We talked about the weekend
and sort of vowed to do it again at least once a month. As we pulled up
to the house we could see that our parents were not yet home.
We made out for a few minutes and just to show Fred how much I enjoyed
this weekend, and looked forward to another, I did something I never
thought I would do. I kissed the head of his big hard cock, just the tip
but enough for me, and Fred, to enjoy it. (Maybe some day I will kiss
more that the tip.)
He helped me get my stuff in the house but did not stay, just as he
drove away; my parents drove up.
Kaylin
- 23.05.2022
- 10
- 0
